Multicomponent Reaction (MCR)

Synthesis
One-pot

Aldehydes
Amines
Carboxylic Acids
β -Keto Esters
Isonitriles
Ureas
Thioureas
Dialkyl Phosphites
Benzyne Precursors
Lewis Acids
Ionic Liquids
 Multicomponent Reactions (MCR)
Multicomponent reaction (MCR) is a synthetic methodology in In 1891, an Italian chemist, P. Biginelli has reported the three-
which three or more reactants come together in a single reaction component MCR using β-keto esters such as ethyl acetoacetate
vessel to form a new product. The characteristic aspect of MCRs [A0649], aromatic aldehydes such as benzaldehyde [B2379],
is that the final products contain almost all portions of substrates, and ureas (or thioureas) in the presence of acid catalyst (Brönsted
generating almost no by-products. That makes MCRs an or Lewis acids), affording dihydropyrimidinone derivaties.4)
extremely ideal and eco-friendly reaction system. Target Dihydropyrimidinones have been paid much attention because of
compounds can be obtained in one pot with much fewer steps. their various bioactivities such as anti-inflammatory or anti-
Therefore, MCRs have been paid much attention in various bacterial activities. For an example of pharmaceuticals developed
research fields, such as discovery of lead compounds in by using the reaction, several anti-tubercular agents have been
medicinal chemistry, or combinatorial chemistry. reported as below.5)

There have been a number of reports on MCRs so far, and Examples of Anti-tubercular Agents using Biginelli Reaction
typical examples are described as below.
NO2
1. Strecker reaction N N
O
(Three-component reaction: 3CR)
F N NH
EtO2C H
NH
Strecker Reaction (Amino Acid Synthesis) N O
N O H
H
O NaCN, NH3 NH2 H3O+ NH2

R H R CN R COOH

4. Passerini reaction (3CR)

This reaction was reported by A. Strecker in 1850, and is
Passerini Reaction
extremely famous as the synthesis of α-amino acids. This O R2
H
reaction is an MCR which comprises three components, N
R1 COOH + R2 CHO + R3 NC R1 O R3
aldehydes, hydrogen cyanide, and ammonia as substrates, and O

is recognized as the world’s first MCR.1)

In 1921, an Italian chemist, M. Passerini et al. have reported the
2. Hantzsch dihydropyridine synthesis (3CR) three-component reaction using carboxylic acids, aldehydes,
and isonitriles, affording α-acyloxy amides.6) The Passerini
Hantzsch Dihydropyridine Synthesis
O O R3 O reaction also has been applied into pharmaceutical research, for
O
2 R 2O OR2 example, Hulme et al. have reported the library synthesis of novel
2 R O + + NH3
R3 H
R1 O R1 N R1 norstatine derivatives bearing benzimidazole moieties.7)
H

This reaction was reported by A. R. Hantzsch in 1881, and is the NHBoc

BocHN R2
best-known three-component MCR, which affords 1,4-dihydro- BocHN R2 CN
O
H
NHBoc
R 1
COOH + + N
2) R1
pyridine derivatives using β-keto esters, aldehydes, and ammonia. CHO CH2Cl2, rt, 18 h O
O

For an example, a calcium channel blocker, “Nifedipine”, is also

Passerini Products
synthesized by this reaction.3) H2N R2
NH2
O
H
Acyl Migration
N
R1 O
10% TFA / CH2Cl2, Et3N / MeOH (1 : 3),
rt, 24 h O rt, 2 h

CHO NO2 R1 O
MeO2C + + NH3 MeO2C CO2Me HN R2 O R2 N
NH2
O NO2 H
N 10% TFA / DCE, R1 N N
H
N HO
MW, 100°C, 20 min
H
OH
H O

Nifedipine

3. Biginelli reaction (3CR)

N O N CH3 N
O O
Biginelli reaction N
H
N
H
N
H
N
H N
H
N
H
OH OH OH
MeO
O R3
O
R3 X H+
R2O NR4 CH3
R 2O + + R4
N N
R5
O CH3 N O
Ph
N O
Ph
N
H O
H H R1 N5 X N
N
HN
N N
R1 O (X = O or S) R N
H H
N
H H
N
H H
OH OH OH

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 Multicomponent Reaction (MCR)

OMOM OMe

5. Gröbcke-Blackburn-Bienaymé reaction Me BnO Me

(3CR) CH3 CHO +

O
O
NH2 + MeO NC + I
BocHN MeOH, reflux
OTBDPS
CO2H
Gröbcke-Blackburn-Bienaymé Reaction
R3
NH OMe OMe
H+ Me OBn HO Me
N N MeO
R1 + R2 CHO + R3 NC R1 R2 OAc
H
N I Me
NH2 OMOM NH
NHBoc
N Me
Me CH3 S N
O O
N O H OH
8) O O
Gröbcke-Blackburn-Bienaymé reaction is a three-component O O O
TBDPSO MeO
MCR using aldehydes, isonitriles, and α-aminoazines such as NH
Ugi Products (Y. 90%) HO
2-aminoimidazole or 2-aminopyridine in the presence of acid
Ecteinascidin 743
catalyst. The reaction is applicable for the synthesis of fused
nitrogen-containing aromatic compounds as below.
Other examples of MCR
N N
N
●MCR using p-toluenesulfonylmethyl isocyanide
N S N
N N
(TosMIC) (3CR)
N NHBn
NHBn
NHBn
p-Toluenesulfonylmethyl isocyanide (TosMIC) [T1046] is a
synthetic reagent, developed by Leusen et al., and has both an
isonitrile group and a tosyl group (leaving group) in one
6. Kabachnik-Fields reaction (3CR) molecule.13) Different from other isonitrile compounds with odor

Kabachnik-Fields Reaction
character, TosMIC is an odorless and solid compound. Because
R2 of its easy-handling property, TosMIC has been widely used for
O O HN
OR3 O
+ R2 NH2 + H P OR3 the synthesis of nitrogen-containing aromatic heterocyclic
R1 H OR3 R1 P
OR3 14)
compounds, such as oxazoles. TosMIC also has been used
for MCRs, for example, Tsoleridis et al. have reported the
In 1952, M. I. Kabachinik et al. have reported the three-component synthesis of quinoxaline derivatives via the three-component
MCR using aldehydes, amines, and dialkyl phosphites in the condensation of o-phenylenediamines, aromatic aldehydes and
presence of acid catalyst (Brønsted or Lewis acids), affording TosMIC.15)
9)
α-aminophosphonates. In recent years, much attention has been
paid to α-aminophoshonates since they can be considered as R1 NH2 O
structural analogues of the corresponding α-amino acids and + ArCHO + CH3 S CH2NC
R2 NH2 O
transition state mimics of peptide hydrolysis. Thus, α-amino-
TosMIC [T1046]
phoshonates have been applied into several research areas, such
as development of renin inhibitors or HIV protease inhibitors.10) R1 N Ar
Base

7. Ugi reaction (4CR) Toluene, reflux, 4 h R2 N

Ugi Reaction
Entry R1 R2 Ar Base Quinoxaline (Y. %)

O R 2 1 H H phenyl DABCO 91
O
R3 N R4
R1 H
+ R2 NH2 + R3 NC + R4 COOH N 2 H H 2,4-dimethylphenyl DABCO 81
H
R1 O
3 H H 4-chlorophenyl DABCO 84

4 Me Me phenyl DBU 86
This reaction is the four-component MCR reported by I. K. Ugi et
5 Me Me 2-methylphenyl DBU 85
al. in 1962 for the first time.11) It enables one-pot condensation of
four components (aldehydes, amines, isonitriles, and carboxylic
acids), thus, it can be said that the Ugi reaction is the most versatile ●MCR using benzynes (3CR)
among MCRs. For an example of applications using this reaction, Recently, there also have been several reports on MCRs using
Fukuyama et al. have reported the synthesis of a marine tunicate, benzynes. For example, Yoshida et al. have reported the three-
Ecteinascidin 743, which has extremely potent antitumor acitivity, component MCR using in situ generated benzynes, imines, and
using the Ugi reaction as a key step below.12) carbon dioxide, affording benzoxadinones.16) Recently, much
attention has been paid on organic synthesis using carbon
dioxide as a carbon source from the ecological point of view,
thus, the reaction above is an extremely useful and eco-friendly
MCR.

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Multicomponent Reaction (MCR)

KF Me TCI offers a variety of aldehyde, amine, carboxylic acid, β-keto

TMS NMe 18-Crown-6 N Ar
R + + CO2 R ester, urea, thiourea, and dialkyl phosphite compounds readily
Ar H O
OTf THF, 0 °C
available in MCRs. For aldehyde, amine, and carboxylic acid
Benzyne Precursor O
Ar = 2,4,6-trimethyphenyl compounds, typical products selected are listed judging from
reports on MCRs so far. In addition, benzyne precursors, Lewis
Benzyne Precursor Reaction time (h) Product acids, and ionic liquids used in MCRs are also listed in this
Me
TMS N Ar brochure.
15
O
OTf
[T2089] O (Y. 82%)

Me Me
F TMS N Ar F N Ar
63
O and O
OTf F
O (Y. 63%, 4 : 1) O
References
OMe
TMS
Me
N Ar 1) A. Strecker, Ann. 1850, 75, 27.
46
OTf
O 2) A. Hantzsch, Ber. 1881, 14, 1637.
[M1884] (Y. 73%)
OMe O 3) R. Alajarin, J. J. Vaquero, J. L. G. Navio, J. A-Builla, Synlett 1992, 297; R. Alajarin,
Me
TMS N Ar P. Jordan, J. J. Vaquero , J. A-Builla, Synthesis, 1995, 389; B. M. Khadilkar, A. A.
60
OTf
O Chitnavis, Ind. J. Chem. 1995, 34B, 652; B. M. Khadilkar, V. G. Gaikar, A. A.
[T2466] O (Y. 44%)
Chitnavis, Tetrahedron Lett. 1995, 36, 8083.
Thus, MCR is a strong synthetic methodology to enable 4) P. Biginelli, Ber. 1891, 24, 1317; P. Biginelli, Ber. 1891, 24, 2962.
condensation of various substrates in one pot, however, in 5) A. R. Trivedi, V. R. Bhuva, B. H. Dholariya, D. K. Dodiya, V. B. Kataria, V. H.
some cases, reactions require long times for completion or Shah, Bioorg. Med. Chem. Lett. 2010, 20, 6100; V. Virsodia, R. R. S. Pissurlenkar,
result in undesired side reactions even after optimization of D. Manvar; C. Dholakia, P. Adlakha, A. Shah, E. Coutinho, Eur. J. Med. Chem.
reaction conditions such as solvents or Lewis acid catalysts. For 2008, 43, 2103
resolving these problems, there have been some successful 6) M. Passerini, Gazz. Chim. Ital. 1921, 51, 181.
reports on accelerating MCRs. For example, Shaabani et al. 7) A. Y. Shaw, F. Medda, C. Hulme, Tetrahedron Lett. 2012, 53, 1313.
have reported the ionic liquid promoted Gröbcke-Blackburn- 8) K. Gröbke, L. Weber, F. Mehlin, Synlett, 1998, 661; C. Blackburn, B. Guan, K.
17)
Bienaymé reaction. As indicated in the table below, in the Shiosaki, S. Tsai, Tetrahedron Lett. 1998, 39, 3635; H. Bienaymé, K. Bouzid,
case of using ionic liquids as solvents, reactions proceed Angew. Chem. 1998, 110, 2349; H. Bienaymé, K. Bouzid, Angew. Chem. Int. Ed.
smoothly to afford the desired products in excellent yields. On 1998, 39, 2234.
the other hand, the yield of product is poor even in the prolonged 9) M. I. Kabachnik, T. Y. Medved, Dokiady Akademii Nauk SSSR, 1952, 83, 689; E.
reaction time (Entry 2). Moreover, as indicated in Entry 1, the K. Fields, J. Am. Chem. Soc. 1952, 74, 1528.
ionic liquid can be reused for the same reactions, maintaining 10) S. Shibuya, YAKUGAKU ZASSHI 2004, 124, 725; M. C. Allen, W. Fuhrer, B. Tuck,
the high yields. R. Wade, J. M. Wood, J. Med. Chem. 1989, 32, 1652; M. K. Manthey, D. T. C.
Huang, W. A. Bubb, R. I. Christpherson, J. Med. Chem. 1998, 41, 4550.
11) I. Ugi, Angew. Chem. Int. Ed. 1962, 1, 8.
R1
N [bmim]Br HN
+ R2 CHO + NC 12) A. Endo, A. Yanagisawa, M. Abe, S. Tohma, T. Kan, T. Fukuyama, J. Am. Chem.
R1
NH2 rt, 3 h N
R2 Soc. 2002, 124, 6552.
N
CH3
N 13) A. M. V. Leusen, Org. Synth. 1977, 57, 102.
Br
[bmim]Br = N 14) O. Possel, A. M. V. Leusen, Heterocycles, 1977, 7, 77; A. M. V. Leusen, O. H.
(CH2)3CH3
[B2193]
Oldenziel, Tetrahedron Lett. 1972, 23, 2373.
15) C. Neochoritis, J. Stephanidou-Stephanatou, C. A. Tsoleridis, Synlett 2009,
Entry R1 R2 Yield (%)
302.
1 Br Ph 98 (95, 92, 90, 85) a

2 Me Ph 98
16) H. Yoshida, H. Fukushima, J. Ohshita, A. Kunai, J. Am. Chem. Soc. 2006, 128,

2' b Me Ph 25 11040.

3 Me 4-CH3C6H4 99 17) A. Shaabani, E. Soleimani, A. Maleki, Tetrahedron Lett. 2006, 47, 3031.

4 Me 4-O2NC6H4 92

5 Me 4-Pyridyl 97

a
The same ionic liquid is used for each of the five runs.
b
Ionic liquid is not used. Reaction time is 12 h.

Ionic liquids can be generally recovered and recycled, which

can help to reduce the waste of traditional solvents which are
rarely reused. In addition, ionic liquids have attracted much
attention as excellent solvents due to their low volatility. Judging
from these points, this reaction can be regarded as a more eco-
friendly reaction example.

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 Multicomponent Reaction (MCR)

P0498 25mL 500mL B0751 25mL 500mL I0101 25mL 500mL

O O O

Aldehydes CH3
H CH3 H
CH3
H
CH3
Propionaldehyde Butyraldehyde Isobutyraldehyde
CAS RN: 123-38-6 CAS RN: 123-72-8 CAS RN: 78-84-2
P0847 5mL 25mL I0192 25mL 100mL 500mL V0001 25mL 500mL H0133 25mL 100mL 500mL H0025 25mL 500mL

H 3C O O O O
CH3 O
H 3C C C H CH3 CH3
CH3 H H CH3 H H
H 3C

Pivalaldehyde Isovaleraldehyde Valeraldehyde Hexanal Heptanal

CAS RN: 630-19-3 CAS RN: 590-86-3 CAS RN: 110-62-3 CAS RN: 66-25-1 CAS RN: 111-71-7
N0296 25mL 100mL 500mL D0032 25mL 500mL U0009 25mL 250mL D0979 25mL 500mL T0410 5mL

O O O O O
CH3 CH3 CH3
H H3C H H CH3 H H

Dodecanal (stabilized with

Nonanal Decanal Undecanal DL-α-Tocopherol) Tridecanal
CAS RN: 124-19-6 CAS RN: 112-31-2 CAS RN: 112-44-7 CAS RN: 112-54-9 CAS RN: 10486-19-8
T2696 1g P1869 1g E0069 25mL 100mL 500mL E0125 25mL 500mL C1707 1g 5g

O O
O O
CH3 H CH3 H
CH3(CH2)12 C H CH3(CH2)13 C H C H
CH3 CH3 O
Tetradecanal Pentadecanal 2-Ethylbutyraldehyde 2-Ethylhexanal Cyclopropanecarboxaldehyde
CAS RN: 124-25-4 CAS RN: 2765-11-9 CAS RN: 97-96-1 CAS RN: 123-05-7 CAS RN: 1489-69-6
C3019 1mL 5mL C0880 25mL 100mL C0881 25mL N0504 5mL 25mL B5279 200mg 1g
O H O H
O
C H
C H
O H O
Cyclopentanecarboxaldehyde 3-Cyclohexene- 5-Norbornene- Bicyclo[2.2.2]oct-5-ene-
(stabilized with HQ) Cyclohexanecarboxaldehyde 1-carboxaldehyde 2-carboxaldehyde 2-carboxaldehyde
CAS RN: 872-53-7 CAS RN: 2043-61-0 CAS RN: 100-50-5 CAS RN: 5453-80-5 CAS RN: 38259-00-6
B2379 500g T0566 25g 100g 500g T0259 25mL 100mL 500mL H0197 25g 100g 500g H0198 25g 100g 500g
O O O
O H O H
C H C H C H
CH3

OH
CH3 OH
Benzaldehyde o-Tolualdehyde p-Tolualdehyde 3-Hydroxybenzaldehyde 4-Hydroxybenzaldehyde
CAS RN: 100-52-7 CAS RN: 529-20-4 CAS RN: 104-87-0 CAS RN: 100-83-4 CAS RN: 123-08-0
C0443 5g 25g C0352 25mL 500mL P0217 25g 100g I0153 25g 250g T0010 25g 100g 500g
O O
O H C H
C H O O

H H
H
C H
CN O O
4-Cyanobenzaldehyde trans-Cinnamaldehyde 3-Phenylpropionaldehyde Isophthalaldehyde Terephthalaldehyde
CAS RN: 105-07-7 CAS RN: 14371-10-9 CAS RN: 104-53-0 CAS RN: 626-19-7 CAS RN: 623-27-8
A0479 25g 100g 500g A0478 25mL 100mL A0480 25mL 500mL D0564 25g 100g 500g C0561 25g 500g
O O O O O
C H C H C H C H C H
OCH3 OH Cl

OCH3
OCH3 OH
o-Anisaldehyde m-Anisaldehyde p-Anisaldehyde 2,4-Dihydroxybenzaldehyde 2-Chlorobenzaldehyde
CAS RN: 135-02-4 CAS RN: 591-31-1 CAS RN: 123-11-5 CAS RN: 95-01-2 CAS RN: 89-98-5

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Multicomponent Reaction (MCR)

C0124 25g 100g 500g C0125 25g 100g 500g T1368 25mL N0130 25g 100g 500g N0129 25g 500g
O O O O O
C H C H C H C H C H
CH3 CH3 NO2

Cl NO2
Cl CH3
3-Chlorobenzaldehyde 4-Chlorobenzaldehyde 2,4,6-Trimethylbenzaldehyde 2-Nitrobenzaldehyde 3-Nitrobenzaldehyde
CAS RN: 587-04-2 CAS RN: 104-88-1 CAS RN: 487-68-3 CAS RN: 552-89-6 CAS RN: 99-61-6
N0559 25g 100g 500g N0002 25mL 100mL 500mL N0003 5g 25g C1465 1g 5g B2019 1g 5g
O O O
C H C H O C H O
C H Cl H C O

O
NO2 F 3,4-Ethylenedioxy-
4-Nitrobenzaldehyde 1-Naphthaldehyde 2-Naphthaldehyde 2-Chloro-4-fluorobenzaldehyde benzaldehyde
CAS RN: 555-16-8 CAS RN: 66-77-3 CAS RN: 66-99-9 CAS RN: 84194-36-5 CAS RN: 29668-44-8
T1281 25g T1399 5g 25g T1091 5g 25g 250g D1666 25g B0242 5g 25g 250g
O O O
O
C H
C H C H C H
CF3 Cl O
C H
CF3 CF3 Cl
2-(Trifluoromethyl)- 3-(Trifluoromethyl)- 4-(Trifluoromethyl)-
benzaldehyde benzaldehyde benzaldehyde 2,3-Dichlorobenzaldehyde 4-Phenylbenzaldehyde
CAS RN: 447-61-0 CAS RN: 454-89-7 CAS RN: 455-19-6 CAS RN: 6334-18-5 CAS RN: 3218-36-8
B0836 25g 100g 500g B0548 25g 100g 500g B0549 25g 250g P0746 5g 25g T2651 5g 25g
O O O O O
C H C H C H C H C H
Br F F CH3O OCH3

Br F F
Br F OCH3
2-Bromobenzaldehyde 3-Bromobenzaldehyde 4-Bromobenzaldehyde Pentafluorobenzaldehyde 2,4,6-Trimethoxybenzaldehyde
CAS RN: 6630-33-7 CAS RN: 3132-99-8 CAS RN: 1122-91-4 CAS RN: 653-37-2 CAS RN: 830-79-5
P0425 25g 100g 500g N0090 25mL 100mL I0143 25mL T0725 25mL 100mL 500mL F0073 25g 500g
O H
O
C H
H
O S H
O
N C H N N O
O
2-Thiophenecarboxaldehyde
2-Pyridinecarboxaldehyde 3-Pyridinecarboxaldehyde 4-Pyridinecarboxaldehyde (stabilized with HQ) Furfural
CAS RN: 1121-60-4 CAS RN: 500-22-1 CAS RN: 872-85-5 CAS RN: 98-03-3 CAS RN: 98-01-1
P0911 5mL 25mL A0219 25mL 500mL I0165 25mL 500mL

CH3

Amines HC CCH2NH2
CH2
NH2 CH3 NH2

Propargylamine Allylamine Isopropylamine

CAS RN: 2450-71-7 CAS RN: 107-11-9 CAS RN: 75-31-0
B0709 25mL 100mL 500mL B0707 25mL 500mL I0095 25mL 500mL A1859 5g 25g A0432 25g 500g

NH2 NH2
CH3 N
CH3
CH3 NH2 CH3 NH2 NH2 N N
N N
CH3 CH3 H H

tert-Butylamine Butylamine Isobutylamine 3-Aminopyrazole 3-Amino-1,2,4-triazole

CAS RN: 75-64-9 CAS RN: 109-73-9 CAS RN: 78-81-9 CAS RN: 1820-80-0 CAS RN: 61-82-5
C0887 25mL 500mL A0445 25mL 100mL 500mL A0463 500g A0411 25g 100g 500g A0989 5g 25g

NH2
N
CH3
NH2
N NH2
NH2 N NH2

Cyclopentylamine Amylamine Aniline 2-Aminopyridine 2-Aminopyrazine

CAS RN: 1003-03-8 CAS RN: 110-58-7 CAS RN: 62-53-3 CAS RN: 504-29-0 CAS RN: 5049-61-6

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 Multicomponent Reaction (MCR)

A0412 25g F0091 25mL 100mL 500mL C0494 25mL 500mL A0633 25g 100g 500g A1060 5g 25g

NH2
N N N
N
O CH2NH2 S NH2 NH2
N NH2 S

2-Aminopyrimidine Furfurylamine Cyclohexylamine 2-Aminothiazole 2-Amino-1,3,4-thiadiazole

CAS RN: 109-12-6 CAS RN: 617-89-0 CAS RN: 108-91-8 CAS RN: 96-50-4 CAS RN: 4005-51-0
B0406 25mL 500mL A1161 25g 250g P0085 25mL 100mL 500mL A0850 5g 25g B0541 25g 250g

CH2NH2 CH2CH2NH2 NH2

N Br
NH2
N CH2NH2 N
H

Benzylamine 2-Picolylamine 2-Phenylethylamine 2-Aminobenzimidazole 2-Bromoaniline

CAS RN: 100-46-9 CAS RN: 3731-51-9 CAS RN: 64-04-0 CAS RN: 934-32-7 CAS RN: 615-36-1
F0513 300mL A2035 300mL A0141 25g 500g

O O O

Carboxylic Acids H OH CH3 OH

CH2
OH

Acrylic Acid
Formic Acid Acetic Acid (stabilized with MEHQ)
CAS RN: 64-18-6 CAS RN: 64-19-7 CAS RN: 79-10-7
P0500 25mL 500mL B0754 25mL 500mL C0439 25g 500g M0052 25g 500g C2123 25g 500g

O O O O
O
CH3 NC HS
OH CH3 OH OH OH ClCH2 C OH

Propionic Acid Butyric Acid Cyanoacetic Acid Thioglycolic Acid Chloroacetic Acid
CAS RN: 79-09-4 CAS RN: 107-92-6 CAS RN: 372-09-8 CAS RN: 68-11-1 CAS RN: 79-11-8
B0531 25g 500g P0497 5g 25g C0387 25mL 100mL 500mL C0888 10g 25g C0512 5g 25g

O
O
O C OH
Br
OH HC C C OH
O OH O OH

Bromoacetic Acid Propiolic Acid Cyclopropanecarboxylic Acid Cyclobutanecarboxylic Acid Cyclopentanecarboxylic Acid
CAS RN: 79-08-3 CAS RN: 471-25-0 CAS RN: 1759-53-1 CAS RN: 3721-95-7 CAS RN: 3400-45-1
C0470 25g 500g B2635 25g 500g H0206 25g 500g F0112 25g P0610 5g 25g
O O O
O OH
C OH C OH C OH
OH
O
C C
OH
F
Cyclohexanecarboxylic Acid Benzoic Acid 2-Hydroxybenzoic Acid 4-Fluorobenzoic Acid Phenylpropiolic Acid
CAS RN: 98-89-5 CAS RN: 65-85-0 CAS RN: 69-72-7 CAS RN: 456-22-4 CAS RN: 637-44-5
C0353 25g 100g 500g P0281 25g 100g 500g A1075 5g N0155 25g 500g B3764 5g 25g
O O
O O C OH C OH O
C OH C CH3 NO2 HO C O
OH
O
C H O
O 1,4-Benzodioxane-
trans-Cinnamic Acid Phthalaldehydic Acid 2-Acetylbenzoic Acid 2-Nitrobenzoic Acid 6-carboxylic Acid
CAS RN: 140-10-3 CAS RN: 119-67-5 CAS RN: 577-56-0 CAS RN: 552-16-9 CAS RN: 4442-54-0
T1145 5g 25g B0552 25g 100g 500g D0869 25g 100g 500g I0053 25g 100g 500g I0054 5g 25g
O O O O
C OH
C OH C OH C OH
Br O I
CH C OH

CF3
4-(Trifluoromethyl)- I
benzoic Acid 2-Bromobenzoic Acid Diphenylacetic Acid 2-Iodobenzoic Acid 4-Iodobenzoic Acid
CAS RN: 455-24-3 CAS RN: 88-65-3 CAS RN: 117-34-0 CAS RN: 88-67-5 CAS RN: 619-58-9

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Multicomponent Reaction (MCR)

A0650 25g 500g A0649 25g 500g M2315 5g 25g

O O O O O O

β-Keto Esters CH3 OCH3 CH3 O CH3 CH3O Cl

Methyl Acetoacetate Ethyl Acetoacetate Methyl Malonyl Chloride

CAS RN: 105-45-3 CAS RN: 141-97-9 CAS RN: 37517-81-0
A1981 25g 500g M2277 5g 25g M0799 25g 100g 500g K0035 25g 100g 500g K0031 5g 25g

O
O O O O O O O O
CH2 O CH3
CH3 CH3
CH3 O OCH3 OCH3 O CH3
O O CH3
Methyl 3-Cyclopropyl- Meldrum's Acid (=2,2-Dimethyl-
Allyl Acetoacetate 3-oxopropionate 1,3-dioxane-4,6-dione) Methyl 3-Oxovalerate Ethyl 3-Oxovalerate
CAS RN: 1118-84-9 CAS RN: 32249-35-7 CAS RN: 2033-24-1 CAS RN: 30414-53-0 CAS RN: 4949-44-4
I0826 25g 500g A0817 25mL E0484 5g 25g A0815 25mL A0816 25mL 100mL 500mL

O O CH3 O O O O O O CH3
O O CH3
CH3 CH3
CH3 O CH3 CH3 O CH3 O Cl CH3 O CH3 C CH2 C O C CH3
CH3

Isopropyl Acetoacetate Propyl Acetoacetate Ethyl Malonyl Chloride sec-Butyl Acetoacetate tert-Butyl Acetoacetate
CAS RN: 542-08-5 CAS RN: 1779-60-8 CAS RN: 36239-09-5 CAS RN: 13562-76-0 CAS RN: 1694-31-1
A0795 25mL E0882 5g 25g K0037 25mL 500mL K0030 25mL 500mL A0814 25mL

O O O O O O O O O O
CH3 CH3
CH3 O CH3 O CH3 CH3 OCH3 CH3 O CH3 CH3 O
CH3 CH3

Butyl Acetoacetate Ethyl Isobutyrylacetate Methyl 3-Oxohexanoate Ethyl 3-Oxohexanoate Isobutyl Acetoacetate
CAS RN: 591-60-6 CAS RN: 7152-15-0 CAS RN: 30414-54-1 CAS RN: 3249-68-1 CAS RN: 7779-75-1
A1583 25g 500g C0911 25g 500g A0811 25mL 500mL D1891 5mL 25mL O0216 10g 25g

O O O O O O
O O O O

OCH3 Cl CH3 CH3

CH3 O O CH3 CH3 O (CH3)3C O CH3 O CH3

2-Methoxyethyl Acetoacetate Ethyl 4-Chloroacetoacetate Amyl Acetoacetate Ethyl 4,4-Dimethyl-3-oxovalerate Ethyl 3-Oxoheptanoate
CAS RN: 22502-03-0 CAS RN: 638-07-3 CAS RN: 6624-84-6 CAS RN: 17094-34-7 CAS RN: 7737-62-4
A0812 25mL 500mL A0813 25mL T0810 25g 100g 500g A0913 25mL O0073 5g 25g

CH3
O O CH3 O O O O O O O O
CH3 CH3 O
CH3 O CH3 CH3 O O CH3
CF3 O CH3 CH3 O CH3
O

Isoamyl Acetoacetate 3-Pentyl Acetoacetate Ethyl 4,4,4-Trifluoroacetoacetate Hexyl Acetoacetate Diethyl Oxalacetate
CAS RN: 2308-18-1 CAS RN: 13562-81-7 CAS RN: 372-31-6 CAS RN: 13562-84-0 CAS RN: 108-56-5
A1080 25mL 100mL 500mL B0097 25g 100g 500g F0435 1g 5g 25g E0489 25g 500g A0915 25mL

O O O O O
O O
O O CH2 O CH3
O CH3 O CH3
CH3 O O CH3 F CCH2C OCH2CH3 CH3 O O
Ethylene Glycol Monoaceto-
acetate Monomethacrylate
Benzyl Acetoacetate Ethyl Benzoylacetate Ethyl (4-Fluorobenzoyl)acetate (stabilized with BHT) n-Octyl Acetoacetate
CAS RN: 5396-89-4 CAS RN: 94-02-0 CAS RN: 1999-00-4 CAS RN: 21282-97-3 CAS RN: 16436-00-3
M1380 5g 25g O0229 1g 5g T1285 10g 25g P1062 5g N0513 5g 25g

O O O O O O
O O
O O O
O CH3 O CH3
CH3 O O CH3
Cl3C O CH3 CF3CF2 O CH3
CH3O O2N

Ethyl Ethyl Ethyl 4,4,5,5,5-Pentafluoro-

4-Methoxybenzoylacetate Diethyl 3-Oxopimelate 4,4,4-Trichloroacetoacetate 3-oxovalerate Ethyl 4-Nitrobenzoylacetate
CAS RN: 2881-83-6 CAS RN: 40420-22-2 CAS RN: 3702-98-5 CAS RN: 663-35-4 CAS RN: 838-57-3

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 Multicomponent Reaction (MCR)

N0875 5g 25g E0759 25g E0811 5g 25g H0828 1g 5g

F O O
O O F O O
O CH3 O O
F
CH3 O O CH3 HO C CH2 C OCH3
F
NO2 Cl N Cl
F
Ethyl (2,3,4,5-Tetrafluoro- Ethyl 3-(2,6-Dichloro-5-fluoro- Methyl (4-Hydroxybenzoyl)-
4-Nitrobenzyl Acetoacetate benzoyl)acetate 3-pyridyl)-3-oxopropionate acetate
CAS RN: 61312-84-3 CAS RN: 94695-50-8 CAS RN: 96568-04-6 CAS RN: 32066-29-8
B1274 5mL 25mL C1438 1g 5g I0562 5g 25g

NC
O
CH3
Isonitriles CH3 C NC
CN
O CH3
CH3
tert-Butyl Isocyanide Cyclohexyl Isocyanide Ethyl Isocyanoacetate
CAS RN: 7188-38-7 CAS RN: 931-53-3 CAS RN: 2999-46-4
B2185 1g 5g T1054 1mL 5mL I0455 1g 5g I0824 1g 5g T1046 5g 25g

CH2NC CH3 CH3 N NC O

N
CH3 C CH2 C NC N
CH3 S CH2NC

CH3 CH3 O
NC
1,1,3,3-Tetramethylbutyl 1(1H-Benzotriazol-1-yl)- p-Toluenesulfonylmethyl
Benzyl Isocyanide Isocyanide methyl Isocyanide 1-Adamantyl Isocyanide Isocyanide (= TosMIC)
CAS RN: 10340-91-7 CAS RN: 14542-93-9 CAS RN: 87022-42-2 CAS RN: 22110-53-8 CAS RN: 36635-61-7
U0073 300g M0455 25g 500g D0289 25g 500g

O O O

Ureas H 2N NH2 H2N NHCH3

CH3
N
H
N
H
CH3

Urea 1-Methylurea 1,3-Dimethylurea

CAS RN: 57-13-6 CAS RN: 598-50-5 CAS RN: 96-31-1
E0192 25g 500g A0237 25g A0124 25g H0700 25g A0101 25g

O O O O O O O
CH2 HO CH3
CH3 N NH2 N NH2 CH3 N NH2 N NH2 CH3 N N
H H H H H H

Ethylurea Allylurea Acetylurea 2-Hydroxyethylurea 1-Acetyl-3-methylurea

CAS RN: 625-52-5 CAS RN: 557-11-9 CAS RN: 591-07-1 CAS RN: 2078-71-9 CAS RN: 623-59-6
B1831 25g D0534 25g 500g D5170 1g 5g H0655 25g D0767 25g 500g

O O O O O
H
CH2 CH2 H 2N N
CH3 N NH2 CH3 N N CH3 N N OH HO N N OH
H H H H H H H
O
1,3-Bis(hydroxymethyl)-
Butylurea 1,3-Diethylurea 1,3-Diallylurea N-Carboxymethylurea urea
CAS RN: 592-31-4 CAS RN: 623-76-7 CAS RN: 1801-72-5 CAS RN: 462-60-2 CAS RN: 140-95-4
C0173 25g C1101 25g 250g C2034 25g B0449 25g T0802 25g

O O O O O
Cl NC O
N NH2 N NH2 N NH2 N NH2
H H H H
N NH2
H
CH3
2-Chloroethylurea Cyanoacetylurea Cyclohexylurea Benzylurea o-Tolylurea
CAS RN: 6296-42-0 CAS RN: 1448-98-2 CAS RN: 698-90-8 CAS RN: 538-32-9 CAS RN: 614-77-7
T0328 25g H0438 25g B4529 1g 5g B1103 25g C0031 25g 100g 500g

O
CH3 Cl Cl
O O O (CH3)3Si Si(CH3)3 O
N N
N NH2 HO N NH2 N N H H N N
H H H H H H

p-Tolylurea 3-Hydroxyphenylurea 1,3-Bis(4-chlorophenyl)urea N,N'-Bis(trimethylsilyl)urea 1,3-Diphenylurea

CAS RN: 622-51-5 CAS RN: 701-82-6 CAS RN: 1219-99-4 CAS RN: 18297-63-7 CAS RN: 102-07-8

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Multicomponent Reaction (MCR)

T2890 5g B2833 5g B2834 5g T1915 25g 250g B2842 25g

O
SO2NH C NH2
CH3 O O
Br O OCH3
O O
H2N C NH(CH2)3 Si OCH3 CH3 N NH2
N NH2 N NH2 OCH3 H
H H Br
CH3 Br 1-[3-(Trimethoxysilyl)-
p-Toluenesulfonylurea (2-Bromophenyl)urea (4-Bromophenyl)urea propyl]urea 1-(2-Bromoisovaleryl)urea
CAS RN: 1694-06-0 CAS RN: 13114-90-4 CAS RN: 1967-25-5 CAS RN: 23843-64-3 CAS RN: 496-67-3
D0441 25g 500g C2266 5g C0926 5g U0048 25mL C1220 25g
O

O O O SO2NH C NHCH2CH2CH3
S
O N NH2 O N O OCH2CH3
H H2N C NH(CH2)3 Si OCH2CH3
N N Cl N N Cl OCH2CH3
H H H H Cl
(4-Chlorophenylsulfonyl)- 1-(2-Chloro-4-pyridyl)- 1-[3-(Triethoxysilyl)propyl]- 1-(4-Chlorophenylsulfonyl)-
1,3-Dicyclohexylurea urea 3-phenylurea urea (40-52% in Methanol) 3-propylurea
CAS RN: 2387-23-7 CAS RN: 22663-37-2 CAS RN: 68157-60-8 CAS RN: 23779-32-0 CAS RN: 94-20-2
O0209 10g T1015 25g 500g I0665 25g 250g E1171 200mg 1g B4483 1g 5g

O CH3CH2O CH3O OCH3

Cl Cl H H H H O O
O HOCH2 N N N N CH2OH
CH3(CH2)17 N N
N NH2 O N O
O O
O N O N N
H N N Cl H H N NH2 H H
H H H
1,3-Bis(4-methoxyphenyl)-
N-Octadecylurea 3,4,4'-Trichlorodiphenylurea Imidazolidinyl Urea (4-Ethoxyphenyl)urea urea
CAS RN: 2158-08-9 CAS RN: 101-20-2 CAS RN: 39236-46-9 CAS RN: 150-69-6 CAS RN: 1227-44-7
T2475 300g M0619 25g 100g D0804 25g 100g 500g

S S S

Thioureas H 2N NH2
CH3
N
H
NH2
CH3
N
H
N
H
CH3

Thiourea N-Methylthiourea 1,3-Dimethylthiourea

CAS RN: 62-56-6 CAS RN: 598-52-7 CAS RN: 534-13-4
A0220 25g 100g 500g B4612 1g 5g A0117 25g 500g G0234 25g 100g 500g D0530 25g 500g

S O S NH S S
S
CH2
N NH2 CH2NH C NH2 CH3 N NH2 H 2N N NH2 CH3 N N CH3
H H H H H

1-Allyl-2-thiourea Benzylthiourea 1-Acetyl-2-thiourea Guanylthiourea 1,3-Diethyl-2-thiourea

CAS RN: 109-57-9 CAS RN: 621-83-0 CAS RN: 591-08-2 CAS RN: 2114-02-5 CAS RN: 105-55-5
P0237 25g 500g D0253 25g T0657 25g B4484 1g 5g C3168 1g 5g

CH3 S CH3 Br
S S S S

N NH2 CH3 N N CH3 N NH2 N NH2 Cl N NH2

H H H H H H
CH3

1-Phenyl-2-thiourea 1,3-Diisopropylthiourea o-Tolylthiourea (4-Bromophenyl)thiourea (3-Chlorophenyl)thiourea

CAS RN: 103-85-5 CAS RN: 2986-17-6 CAS RN: 614-78-8 CAS RN: 2646-30-2 CAS RN: 4947-89-1
T0656 5g F0836 5g 25g D0802 25g B4611 1g 5g D0301 25g 500g

CH3 F CF3 CF3 S

S S S S
CH3 N N CH3
N NH2 N NH2 N N N N H H
H H
H H H H
CH3 CH3
1,3-Bis[4-(trifluoromethyl)-
p-Tolylthiourea (4-Fluorophenyl)thiourea 1,3-Di(o-tolyl)thiourea phenyl]thiourea 1,3-Dibutylthiourea
CAS RN: 622-52-6 CAS RN: 459-05-2 CAS RN: 137-97-3 CAS RN: 1744-07-6 CAS RN: 109-46-6
P1167 5g N0071 5g 25g M2786 1g 5g T0197 25g 500g D0440 5g 25g
S

HN NH2
S NH S S S
NH C NH C NH2 CH3
N N N N N N
H H H H H H

1-Phenyl-3-guanylthiourea 1-(1-Naphthyl)-2-thiourea 1-Methyl-3-phenylthiourea 1,3-Diphenylthiourea 1,3-Dicyclohexylthiourea

CAS RN: 15989-47-6 CAS RN: 86-88-4 CAS RN: 2724-69-8 CAS RN: 102-08-9 CAS RN: 1212-29-9

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 Multicomponent Reaction (MCR)

B0802 25g D0803 5g 25g B3452 200mg 1g B4997 1g 5g B4482 1g

O S CF3 CF3
S CH3O OCH3
CH3 CH3 S
N NH2 S S
H N N N N
N N CF3 N N CF3 H H H H
H H H H

1,3-Bis[3,5-bis(trifluoromethyl)- 1,3-Bis(4-methoxyphenyl)-
N-Benzoylthiourea 1,3-Di(p-tolyl)thiourea phenyl]thiourea 1-Benzyl-3-phenylthiourea thiourea
CAS RN: 614-23-3 CAS RN: 621-01-2 CAS RN: 1060-92-0 CAS RN: 726-25-0 CAS RN: 1227-45-8
P0629 25g 500g D0300 25g D3417 25g 500g

O O
Dialkyl Phosphites
O
CH3 CH3 CH3 CH3
CHO P OCH CH3(CH2)3O P O(CH2)3CH3 CHCH2O P OCH2CH
CH3 CH3 CH3 CH3
H H H

Diisopropyl Phosphite Dibutyl Phosphite Diisobutyl Phosphite

CAS RN: 1809-20-7 CAS RN: 1809-19-4 CAS RN: 1189-24-8
D5814 1g 5g B2627 5g 25g D0907 25g 100g 500g P1016 25g 250g

O O
O O
CF3CH2O O P O CH2O P OCH2
(CH3)3CO P OC(CH3)3 P H H H
CF3CH2O
H
Bis(2,2,2-trifluoroethyl)-
Di-tert-butyl Phosphonate Phosphite Diphenyl Phosphite Dibenzyl Phosphite
CAS RN: 13086-84-5 CAS RN: 92466-70-1 CAS RN: 4712-55-4 CAS RN: 17176-77-1
A1464 1g 5g T2089 1g 5g 25g M1883 1g 5g
OSO2CF3
OSO2CF3
(CH3)3Si CH3
N Si(CH3)3

Benzyne Precursors N
N

2-Methyl-
NH2
2-(Trimethylsilyl)phenyl 6-(trimethylsilyl)phenyl
1-Aminobenzotriazole Trifluoromethanesulfonate Trifluoromethanesulfonate
CAS RN: 1614-12-6 CAS RN: 88284-48-4 CAS RN: 556812-44-3
M1882 1g 5g D2503 5g 25g M1884 1g 5g M1885 1g 5g D3883 1g 5g
OSO2CF3 OSO2CF3 OSO2CF3 OSO2CF3
O
Si(CH3)3 C O
. H 2O Si(CH3)3 Si(CH3)3 Si(CH3)3

I OCH3 CH3O
OCH3
CH3 3-Methoxy- 4-Methoxy- OCH3
4-Methyl-2-(trimethylsilyl)phenyl Diphenyliodonium- 2-(trimethylsilyl)phenyl 2-(trimethylsilyl)phenyl 4,5-Dimethoxy-2-(trimethylsilyl)-
Trifluoromethanesulfonate 2-carboxylate Monohydrate Trifluoromethanesulfonate Trifluoromethanesulfonate phenyl Triflate
CAS RN: 262373-15-9 CAS RN: 96195-89-0 CAS RN: 217813-03-1 CAS RN: 556812-41-0 CAS RN: 866252-52-0
B5557 200mg 1g B5559 1g T2465 1g 5g T2466 1g 5g B5080 1g
C(CH3)3 OSO2CF3

CH3 Si CH3 Si(CH3)3 Si(CH3)3

OSO2CF3 CF3O2SO OSO2CF3
CF3SO3 OSO2CF3 OSO2CF3
(CH3)3Si
(CH3)3Si Si(CH3)3
OSO2CF3 Si(CH3)3
2-(tert-Butyldimethylsilyl)- 2,5-Bis(trimethylsilyl)- 1-(Trimethylsilyl)-2-naphthyl 3-(Trimethylsilyl)-2-naphthyl 3,6-Bis(trimethylsilyl)-
1,3-phenylene Triflate 1,4-phenylene Triflate Trifluoromethanesulfonate Trifluoromethanesulfonate naphthalene-2,7-diyl Ditriflate
CAS RN: 1637638-66-4 CAS RN: 613676-07-6 CAS RN: 252054-88-9 CAS RN: 780820-43-1 CAS RN: 947488-89-3
P1620 1g 5g B3047 1g T2467 1g
OSO2CF3
Si(CH3)3
I OSO2CF3
(CH3)3Si Si(CH3)3
Si(CH3)3
CF3O2SO OSO2CF3 (CH3)3Si

CF3O2SO OSO2CF3
Phenyl[2-(trimethylsilyl)- 3,3'-Bis(trimethylsilyl)- Si(CH3)3
phenyl]iodonium biphenyl-4,4'-diyl 1,3,5-Tris[4-(trifluoromethanesulfonyloxy)-
Trifluoromethanesulfonate Bis(trifluoromethanesulfonate) 3-(trimethylsilyl)phenyl]benzene
CAS RN: 164594-13-2 CAS RN: 828282-80-0 CAS RN: 847925-63-7
L0204 25g 300g L0210 25g 100g 500g N0850 25g 500g

Lewis Acids LiCl LiBr NiCl2

Lithium Chloride
Anhydrous Lithium Bromide Nickel(II) Chloride Anhydrous
CAS RN: 7447-41-8 CAS RN: 7550-35-8 CAS RN: 7718-54-9

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 Z0014 25g 300g B0527 25mL 100mL 500mL T0267 25g 500g T3238 100mL 500mL T2052 100mL 500mL
SO3H

. H 2O
ZnCl2 BF3 . CH3 O CH3 TiCl4 TiCl4
CH3
Boron Trifluoride - Ethyl p-Toluenesulfonic Acid Titanium(IV) Chloride (ca. Titanium(IV) Chloride (14% in
Zinc Chloride Ether Complex Monohydrate 19% in Toluene, ca. 1.0mol/L) Dichloromethane, ca. 1.0mol/L)
CAS RN: 7646-85-7 CAS RN: 109-63-7 CAS RN: 6192-52-5 CAS RN: 7550-45-0 CAS RN: 7550-45-0
R0074 1g 5g I0778 5g 25g B3546 25g 250g T1663 1g 5g T1293 5g 25g

O O

RuCl3 . xH2O InCl3 BiCl3

CF3 S O Sc3 CF3 S O La3
O 3 O 3

Ruthenium(III) Chloride Indium(III) Chloride Bismuth(III) Chloride Scandium(III) Lanthanum(III)

Hydrate Anhydrous Anhydrous Trifluoromethanesulfonate Trifluoromethanesulfonate
CAS RN: 14898-67-0 CAS RN: 10025-82-8 CAS RN: 7787-60-2 CAS RN: 144026-79-9 CAS RN: 52093-26-2
T1610 5g 25g

O
CF3 S O Yb3
O 3

Ytterbium(III)
Trifluoromethanesulfonate
CAS RN: 54761-04-5
B2194 5g 25g 100g B2193 5g B2195 5g 25g 100g
CH3 CH3 CH3
N N N

Ionic Liquids N
(CH2)3CH3
Cl
N
(CH2)3CH3
Br
N
(CH2)3CH3
BF4

1-Butyl-3-methylimidazolium 1-Butyl-3-methylimidazolium 1-Butyl-3-methylimidazolium

Chloride Bromide Tetrafluoroborate
CAS RN: 79917-90-1 CAS RN: 85100-77-2 CAS RN: 174501-65-6
B2320 5g 25g B2337 5g 25g T0055 5g 25g 100g T0054 25g 100g 500g T1124 25g 100g 500g
CH3 CH3
N N (CH2)3CH3 (CH2)3CH3
(CH2)3CH3
PF6 CF3SO3 CH3(CH2)3 N (CH2)3CH3 Cl CH3(CH2)3 N (CH2)3CH3 Br CH3(CH2)3 P (CH2)3CH3 Br
N N
(CH2)3CH3 (CH2)3CH3 (CH2)3CH3
(CH2)3CH3 (CH2)3CH3
1-Butyl-3-methylimidazolium 1-Butyl-3-methylimidazolium Tetrabutylammonium Tetrabutylammonium Tetrabutylphosphonium
Hexafluorophosphate Trifluoromethanesulfonate Chloride Bromide Bromide
CAS RN: 174501-64-5 CAS RN: 174899-66-2 CAS RN: 1112-67-0 CAS RN: 1643-19-2 CAS RN: 3115-68-2

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