Organic Chemistry III

University of Ahel AL-Bait

College of Pharmacy
Second Stage
Second Semester

Lec. 1
Heterocyclic system: Classes,
Structures, Properties, Occurrence
in Nature and in Medicinal Products
Prepared: Assist. Prof. Dr. Atheer Alghanimi
Ph.D. in Chemistry
Edited &Presented: Dr. Dhiaaddin Al -Saadi 1
 Contents of the Course
1. Heterocyclic systems: Classes of heterocyclic systems;
general structures; properties; occurrence in nature and in
medicinal products.

2. Five-membered ring heterocyclic compounds: Pyrrole,

furan and thiophen.

3. Source of pyrrole, furan and thiophen.

4. Electrophilic substitution in pyrrole, furan and thiophen:

Reactivity and orientation.

5. Six-membered ring heterocyclic compounds: Structure &

reactions of pyridine.

6. Saturated five-membered heterocyclic compounds.

7. Heterocyclics of five- & six-membered rings with two &

three heteroatoms.
2
 General Objectives of this course

In this course, the student will be able to:

1. Know about the most important simple heterocyclic ring systems
containing heteroatom and their systems of nomenclature and
numbering.

2. Understand and discuss the reactivity and stability of heter-

aromatic compounds.

3. Study the important synthetic routes and reactivity for five- and
six-membered heteroaromatic compounds.

4. Understand the important physical and chemical properties of

five- and six-membered heteroaromatic compounds.

5. Know about the applications of these heteroaromatic

compounds in the synthesis of important industrial and
pharmaceutical compounds.

3
 Introduction
 Heterocyclic systems: are those where one or more atom(s) of the ring
are heteroatoms. For example: N (Nitrogen), O (Oxygen), S (Sulphur), P
(Phosphorous), As (Arsenic), Se (Selenium), B (Boron), Sb
(Antimony), Bi (Bismuth), Si (Silicon), Sn (Tin), Pb
(Lead), Hg (Mercury), etc. (N = Aza, O = Oxa, S = Thia, P
‫ ھﻲ ﺗﻠﻚ اﻟﺘﻲ ﺗﻜﻮن ﻓﯿﮭﺎ ذرة واﺣﺪة أو أﻛﺜﺮ ﻣﻦ اﻟﺤﻠﻘﺔ ﻋﺒﺎرة ﻋﻦ ذرات‬:‫اﻷﻧﻈﻤﺔ اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ‬
= Phospha) As ، (‫ )ﻓﻮﺳﻔﻮر‬P ، (‫ )ﻛﺒﺮﯾﺖ‬S ، (‫ )أﻛﺴﺠﯿﻦ‬O ، (‫ )ﻧﯿﺘﺮوﺟﯿﻦ‬N :‫ ﻋﻠﻰ ﺳﺒﯿﻞ اﻟﻤﺜﺎل‬.‫ﻏﯿﺮ ﻣﺘﺠﺎﻧﺴﺔ‬
Sn ، (‫ )ﺳﯿﻠﯿﻜﻮن‬Si ، (‫ )ﺑﺰﻣﻮت‬Bi ، (‫ )اﻷﻧﺘﯿﻤﻮن‬Sb ، (‫ )اﻟﺒﻮرون‬B ، (‫ )اﻟﺴﯿﻠﯿﻨﯿﻮم‬Se ، (‫)زرﻧﯿﺦ‬
= N = Aza ، O = Oxa ، S = Thia ، P) .‫ إﻟﺦ‬، (‫ زﺋﺒﻖ )زﺋﺒﻖ‬، (‫ )رﺻﺎص‬Pb ، (‫)ﻗﺼﺪﯾﺮ‬
(‫ﻓﻮﺳﻔﺎ‬
.‫● اﻟﻜﻠﻤﺔ اﻟﯿﻮﻧﺎﻧﯿﺔ "ﻣﻐﺎﯾﺮﯾﻦ" ﺗﻌﻨﻲ ﻣﺨﺘﻠﻔﺔ‬
 The Greek word “heteros” means different. .‫● أﻛﺜﺮ ﻣﻦ ﻧﺼﻒ اﻟﻤﺮﻛﺒﺎت اﻟﻌﻀﻮﯾﺔ اﻟﻤﻌﺮوﻓﺔ ھﻲ ﺣﻠﻘﯿﺔ ﻏﯿﺮ ﻣﺘﺠﺎﻧﺴﺔ‬
‫ ﻣﺴﺘﻘﺮة‬، ‫● اﻟﻤﺮﻛﺒﺎت اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ اﻟﺘﻲ ﺗﺤﺘﻮي ﻋﻠﻰ ذرة ﻏﯿﺮ ﻣﺘﺠﺎﻧﺴﺔ واﺣﺪة ﻋﻠﻰ اﻷﻗﻞ‬
‫ ﺗﺪﻋﻲ ﻣﺼﺎدر أﺧﺮى أن اﻟﻌﻄﺮﯾﺔ ﻟﯿﺴﺖ ﺷﺮطﺎ أﺳﺎﺳﯿﺎ ﻟﺘﺤﺪﯾﺪ اﻟﻤﺮﻛﺒﺎت‬، ‫ وﻣﻊ ذﻟﻚ‬.‫ﻧﺴﺒﯿﺎ وﺗﻈﮭﺮ ﻋﻄﺮﯾﺔ‬
.‫اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ‬

 More than half of the known organic compounds are heterocyclics.

 Heterocyclic compounds that contain at least one hetero-atom, are

relatively stable and show aromaticity. However, other sources claim
that aromaticity is not a prerequisite for defining heterocyclic
compounds. 4
 Importance of heterocyclic compounds

 Heterocyclic compounds are abundant in plants and animal

products; and they are one of the important constituent of
natural organic compounds known. Alkaloids, natural dyes,
‫اﻟﻤﺮﻛﺒﺎت اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ وﻓﯿﺮة ﻓﻲ اﻟﻨﺒﺎﺗﺎت واﻟﻤﻨﺘﺠﺎت‬
‫ وھﻲ واﺣﺪة ﻣﻦ اﻟﻤﻜﻮﻧﺎت اﻟﻤﮭﻤﺔ ﻟﻠﻤﺮﻛﺒﺎت‬.‫اﻟﺤﯿﻮاﻧﯿﺔ‬
drugs, proteins, enzymes, nucleic acids, etc. ، ‫ أﺻﺒﺎغ طﺒﯿﻌﯿﺔ‬، ‫ ﻗﻠﻮﯾﺪات‬.‫اﻟﻌﻀﻮﯾﺔ اﻟﻄﺒﯿﻌﯿﺔ اﻟﻤﻌﺮوﻓﺔ‬
.‫ إﻟﺦ‬، ‫ أﺣﻤﺎض ﻧﻮوﯾﺔ‬، ‫ إﻧﺰﯾﻤﺎت‬، ‫ ﺑﺮوﺗﯿﻨﺎت‬، ‫أدوﯾﺔ‬
‫● اﻟﻤﺮﻛﺒﺎت اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ ﻟﮭﺎ ﺗﻄﺒﯿﻖ واﺳﻊ ﻓﻲ‬
‫اﻟﻤﺴﺘﺤﻀﺮات اﻟﺼﯿﺪﻻﻧﯿﺔ واﻟﻜﯿﻤﺎوﯾﺎت اﻟﺰراﻋﯿﺔ واﻟﻤﻨﺘﺠﺎت‬
 Heterocyclic compounds have a wide application in .‫اﻟﺒﯿﻄﺮﯾﺔ‬
‫● اﻟﻌﺪﯾﺪ ﻣﻦ اﻟﻤﺮﻛﺒﺎت اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ ﻣﻔﯿﺪة ﺟﺪا‬
.‫وﺿﺮورﯾﺔ ﻟﺤﯿﺎة اﻹﻧﺴﺎن‬
‫● ﻣﺮﻛﺒﺎت ﻣﺨﺘﻠﻔﺔ ﻣﺜﻞ اﻟﮭﺮﻣﻮﻧﺎت واﻟﻘﻠﻮﯾﺪات واﻟﻤﻀﺎدات‬
pharmaceuticals, agrochemicals and veterinary products. ‫اﻟﺤﯿﻮﯾﺔ واﻷﺣﻤﺎض اﻷﻣﯿﻨﯿﺔ اﻷﺳﺎﺳﯿﺔ واﻟﮭﯿﻤﻮﺟﻠﻮﺑﯿﻦ‬
‫واﻟﻔﯿﺘﺎﻣﯿﻨﺎت وﻣﻮاد اﻟﺼﺒﻐﺔ واﻷﺻﺒﺎغ ﻟﮭﺎ ھﯿﺎﻛﻞ ﺣﻠﻘﯿﺔ ﻏﯿﺮ‬

 Many heterocyclic compounds are very useful and essential for

human life.

 Various compounds such as hormones, alkaloids, antibiotics,

essential amino acids, hemoglobin, vitamins, dye stuffs and
pigments have heterocyclic structures.
5
 Classification of Cyclic Compounds
Cyclic organic compounds

Heterocyclic Carbocyclic
Compounds Compounds
(H.Cs.) (C.Cs.)

Nonaromatic containing Nonaromatic (Aliphatic, Aromatic and

unsaturated bonds saturated) Unsaturated

Fused-ring Monocyclic
Fused-ring Monocyclic

Monocyclic containing more Monocyclic containing Monocyclic containing Monocyclic containing

than one hetero atom one hetero atom more than one hetero atom one hetero atom
3 membered ring 3 membered ring 3 membered ring 3 membered ring
4 membered ring 4 membered ring 4 membered ring 4 membered ring
5 membered ring 5 membered ring 5 membered ring 5 membered ring
6 membered ring 6 membered ring 6 membered ring 6 membered ring
7 membered ring 7 membered ring 7 membered ring 7 membered ring
6
8 membered ring 8 membered ring
8 membered ring 8 membered ring
6
7
 Aliphatic heterocyclic compounds
 Based on the structural and electronic arrangement, the
heterocyclic compounds may be classified into two categories.
I. Aliphatic heterocyclic compounds. ‫ ﯾﻤﻜﻦ ﺗﺼﻨﯿﻒ اﻟﻤﺮﻛﺒﺎت اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ‬، ‫ﺑﻨﺎء ﻋﻠﻰ اﻟﺘﺮﺗﯿﺐ اﻟﮭﯿﻜﻠﻲ واﻹﻟﻜﺘﺮوﻧﻲ‬
.‫اﻟﻤﺘﺠﺎﻧﺴﺔ إﻟﻰ ﻓﺌﺘﯿﻦ‬
I. ‫اﻟﻤﺮﻛﺒﺎت اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ اﻷﻟﯿﻔﺎﺗﯿﺔ‬.
II. Aromatic heterocyclic compounds. II. ‫اﻟﻤﺮﻛﺒﺎت اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ اﻟﻌﻄﺮﯾﺔ‬.

 Aliphatic heterocycles those do not contain double bonds, and are

called saturated heterocycles.

8
 ‫‪Aromatic heterocyclic compounds‬‬
‫اﻟﻤﺮﻛﺒﺎت اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ اﻟﻌﻄﺮﯾﺔ ﻣﻤﺎﺛﻠﺔ ﻟﻠﺒﻨﺰﯾﻦ ‪ ،‬وﺗﺘﺒﻊ ﻗﺎﻋﺪة ھﺎﻛﻞ‬

‫‪ Aromatic heterocyclic compounds are analogous of benzene,‬‬

‫‪and they follow the Huckel’s rule.‬‬
‫● ﻗﺪ ﺗﺘﻜﻮن اﻟﺤﻠﻘﺔ اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ ﻣﻦ ﺛﻼث أو أﻛﺜﺮ ﻣﻦ ﺛﻼث ذرات ‪ ،‬واﻟﺘﻲ ﻗﺪ ﺗﻜﻮن ﻣﺸﺒﻌﺔ أو ﻏﯿﺮ ﻣﺸﺒﻌﺔ‬

‫‪ A heterocyclic ring may comprise of three or more than three‬‬

‫‪atoms, which may be saturated or unsaturated.‬‬
‫● ﻗﺪ ﺗﺤﺘﻮي اﻟﺤﻠﻘﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ ﻋﻠﻰ أﻛﺜﺮ ﻣﻦ ذرة ﻏﯿﺮ ﻣﺘﺠﺎﻧﺴﺔ ﻗﺪ ﺗﻜﻮن ﻣﺘﺸﺎﺑﮭﺔ أو ﻣﺨﺘﻠﻔﺔ‪.‬‬
‫‪ The heterocyclic ring may contain more than one heteroatom‬‬
‫‪which may be either similar or different.‬‬

‫ﺗﺘﻨﺒﺄ ﻗﺎﻋﺪة ھﺎﻛﻞ ﺑﺄن ﺟﺰﯾﺌﺎت اﻟﺤﻠﻘﺔ اﻟﻤﺴﺘﻮﯾﺔ اﻟﺪورﯾﺔ ﺳﯿﻜﻮن ﻟﮭﺎ‬
‫ﺧﺼﺎﺋﺺ ﻋﻄﺮﯾﺔ إذا ﻛﺎﻧﺖ ﺗﺤﺘﻮي ﻋﻠﻰ إﻟﻜﺘﺮوﻧﺎت ‪4n + 2 pi‬‬
‫)إﻟﻜﺘﺮوﻧﺎت ذات رواﺑﻂ ‪ ، (pi‬ﻋﻨﺪﻣﺎ ﯾﻜﻮن ‪ n‬ﻋﺪدا ﺻﺤﯿﺤﺎ ﻏﯿﺮ‬
‫ﺳﺎﻟﺐ ‪ ،‬أي ﯾﺠﺐ اﻟﺤﺼﻮل ﻋﻠﻰ ﻋﺪد ﻣﻮﺟﺐ وﺻﺤﯿﺢ‪ .‬إﻧﮫ ﻣﻔﯿﺪ ﺟﺪا‬
‫ﻓﻲ ﺗﻘﺪﯾﺮ ﻋﻄﺮﯾﺔ )وﺑﺎﻟﺘﺎﻟﻲ اﺳﺘﻘﺮار( اﻟﺠﺰﯾﺌﺎت ﻋﻠﻰ ﺷﻜﻞ ﺣﻠﻘﺔ‬
‫ﻟﻠﮭﯿﺎﻛﻞ اﻟﻤﺴﺘﻮﯾﺔ‪.‬‬
‫‪9‬‬
 Huckel’s Rule
‫ﺗﺮﺟﻤﺔ‬

 Huckel’s rule predicts that a cyclic, planar ring molecules will have
aromatic properties if it has 4n + 2 pi electrons (electrons with pi bonds),
when n is a non-negative integer, i.e., a positive and whole number must
be obtained. It’s very useful in the estimation of the aromaticity (and ‫● ﻟﻤﺎذا اﻟﺒﻨﺰﯾﻦ ﻣﺴﺘﻘﺮ؟ ﻧﻈﺮا ﻟﻮﺟﻮد‬
therefore the stability) of ring-shaped molecules of planar structures.
 Why is benzene stable? Because there are conjugated delocalized
electrons above and below the plane of the ring, which makes benzene
particularly stable. It resists addition reactions since they would involve
breaking the delocalization and losing that stability. Thus, its aromaticity
is the major contributor to why it’s so unreactive.
 Benzene is less reactive with electrophiles than cyclohexene: Because ‫ﺗﺮﺟﻤﺔ‬

the delocalized pi system in benzene has a lower electron density than

the localized pi bond in the c-c double bond in cyclohexene. This also
means benzene cannot polarize bonds to generate nucleophiles. Thus,
aromatic compounds are more stable than non-aromatic ones because
they have all of their pi electrons in low-energy bonding molecular
orbitals. Also, they can only undergo reactions if the end product keeps
the aromaticity of the ring. Examples of aromatic compounds: pyridine,
10
cyclopentadienyl anion, furan, pyrrole, thiophene, phenol, etc.
 ‫‪Aromaticity of heterocyclic compounds‬‬
‫● اﻟﻤﺮﻛﺒﺎت اﻟﻌﻄﺮﯾﺔ ﻣﺴﺘﻘﺮة ﻟﻠﻐﺎﯾﺔ ﺑﺴﺒﺐ اﺳﺘﻘﺮار اﻟﺮﻧﯿﻦ ﻟﻺﻟﻜﺘﺮوﻧﺎت اﻟﻤﺘﺮاﻓﻘﺔ واﻟﺮواﺑﻂ اﻟﻤﺘﺪاﺧﻠﺔ‪.‬‬

‫‪ Aromatic compounds are very stable due to resonance stability‬‬

‫‪of the conjugated electrons and overlapping  bonds.‬‬
‫اﻟﺒﻨﺰﯾﻦ أﻗﻞ ﺗﻔﺎﻋﻼ ﻣﻊ اﻟﻤﺤﺒﺔ ﻟﻠﻜﮭﺮﺑﺎء ﻣﻦ اﻟﺴﯿﻜﻠﻮھﯿﻜﺴﯿﻦ‪ :‬ﻷن ﻧﻈﺎم ‪pi‬‬
‫ﻏﯿﺮ اﻟﻤﺘﻤﺮﻛﺰ ﻓﻲ اﻟﺒﻨﺰﯾﻦ ﻟﮫ ﻛﺜﺎﻓﺔ إﻟﻜﺘﺮوﻧﯿﺔ أﻗﻞ ﻣﻦ راﺑﻄﺔ ‪ pi‬اﻟﻤﻮﺿﻌﯿﺔ‬
‫ﻓﻲ اﻟﺮاﺑﻄﺔ اﻟﻤﺰدوﺟﺔ ‪ c-c‬ﻓﻲ ‪ .cyclohexene‬ھﺬا ﯾﻌﻨﻲ أﯾﻀﺎ أن‬
‫اﻟﺒﻨﺰﯾﻦ ﻻ ﯾﻤﻜﻨﮫ اﺳﺘﻘﻄﺎب اﻟﺮواﺑﻂ ﻟﺘﻮﻟﯿﺪ اﻟﻨﻮاة‪ .‬وﺑﺎﻟﺘﺎﻟﻲ ‪ ،‬ﻓﺈن اﻟﻤﺮﻛﺒﺎت‬
‫اﻟﻌﻄﺮﯾﺔ أﻛﺜﺮ اﺳﺘﻘﺮارا ﻣﻦ اﻟﻤﺮﻛﺒﺎت ﻏﯿﺮ اﻟﻌﻄﺮﯾﺔ ﻷﻧﮭﺎ ﺗﺤﺘﻮي ﻋﻠﻰ ﺟﻤﯿﻊ‬
‫إﻟﻜﺘﺮوﻧﺎت ‪ pi‬ﻓﻲ ﻣﺪارات ﺟﺰﯾﺌﯿﺔ ﻣﻨﺨﻔﻀﺔ اﻟﻄﺎﻗﺔ‪ .‬أﯾﻀﺎ ‪ ،‬ﻻ ﯾﻤﻜﻨﮭﻢ‬
‫اﻟﺨﻀﻮع ﻟﺮدود ﻓﻌﻞ إﻻ إذا ﻛﺎن اﻟﻤﻨﺘﺞ اﻟﻨﮭﺎﺋﻲ ﯾﺤﺎﻓﻆ ﻋﻠﻰ راﺋﺤﺔ اﻟﺤﻠﻘﺔ‪.‬‬
‫أﻣﺜﻠﺔ ﻋﻠﻰ اﻟﻤﺮﻛﺒﺎت اﻟﻌﻄﺮﯾﺔ‪ :‬اﻟﺒﯿﺮﯾﺪﯾﻦ ‪ ،‬أﻧﯿﻮن ﺳﯿﻜﻠﻮﺑﻨﺘﺎدﯾﻨﯿﻞ ‪،‬‬
‫اﻟﻔﯿﻮران ‪ ،‬اﻟﺒﯿﺮول ‪ ،‬اﻟﺜﯿﻮﻓﯿﻦ ‪ ،‬اﻟﻔﯿﻨﻮل ‪ ،‬إﻟﺦ‪.‬‬

‫‪Look for the following 4 criteria to identify aromatic‬‬

‫‪compound.‬‬
‫ﻛﻠﺶ ﻣﮭﻤﺎت‬

‫‪compounds.‬‬

‫‪11‬‬
 Aromaticity Rules
 Cyclic
‫● دوري‬
.‫دورة أو دوري ﯾﻌﻨﻲ ﺣﻠﻘﺔ‬

Cycle or cyclic implies a ring.

‫● ﻣﺴﺘﻮ‬
‫ ﯾﺠﺐ أن ﺗﺤﺘﻮي اﻟﺤﻠﻘﺔ ﻋﻠﻰ ذراﺗﮭﺎ ﻓﻲ ﻧﻔﺲ‬، ‫ﻧﻈﺮا ﻷن اﻟﻌﻄﺮﯾﺔ ﺗﻌﺘﻤﺪ ﻋﻠﻰ ﻗﺪرة اﻟﻤﺪارات ﻋﻠﻰ اﻟﺘﺪاﺧﻞ‬

Planar .‫اﻟﻤﺴﺘﻮى‬
.‫ﯾﺠﺐ أن ﯾﻜﻮن اﻟﺠﺰيء ﻣﺴﻄﺤﺎ‬

Since aromaticity relies on the ability of orbitals to overlap, the

ring must have its atoms in the same plane.
The molecule must be flat.
sp2 carbons are trigonal planar or simply ‘flat’.

1
 Aromaticity Rules
Conjugated ‫ﻣﺘﺮاﻓﻖ‬
‫ ﻗﺎدرة ﻋﻠﻰ اﻟﺮﻧﯿﻦ )ﻗﺪرة‬SP2 ‫ ذرات‬.‫رﺑﻤﺎ ﺗﻜﻮن ﻗﺪ ﺣﻔﻈﺖ أن اﻷﻧﻈﻤﺔ اﻟﻤﺘﺮاﻓﻘﺔ ﻟﮭﺎ رواﺑﻂ ﻣﻔﺮدة وﻣﺰدوﺟﺔ ﺑﺎﻟﺘﻨﺎوب‬
.(‫ ﻋﻠﻰ إﻟﻐﺎء اﻟﺘﻤﺮﻛﺰ‬Pi ‫ ﻓﻲ ﻣﺪارات‬ES

You may have memorized that conjugated systems have

alternating single and double bonds. sp2 atoms capable of
resonance (ability of the es in the pi orbitals to delocalize).

Huckel’s Rule
Huckel’s Rule: 4n+2 = Number of Resonating or pi Electrons 13
Examples

14
 Properties of Aromatic Compounds (Arenes)
 1. Have extremely high resonance energy (extra stability of the
conjugated system compared to the corresponding number of isolated
‫ ﻟﺪﯾﮭﺎ طﺎﻗﺔ رﻧﯿﻦ ﻋﺎﻟﯿﺔ ﻟﻠﻐﺎﯾﺔ )ﺛﺒﺎت إﺿﺎﻓﻲ ﻟﻠﻨﻈﺎم اﻟﻤﺘﺮاﻓﻖ ﻣﻘﺎرﻧﺔ ﺑﺎﻟﻌﺪد اﻟﻤﻘﺎﺑﻞ ﻣﻦ‬.1
double bonds, i.e., high resonance stability . .‫ أي ﺛﺒﺎت)اﺳﺘﻘﺮار( اﻟﺮﻧﯿﻦ اﻟﻌﺎﻟﻲ‬، ‫اﻟﺮواﺑﻂ اﻟﻤﺰدوﺟﺔ اﻟﻤﻌﺰوﻟﺔ‬
.‫ ھﻲ ﻣﺮﻛﺒﺎت ﻣﺴﺘﻘﺮة ﻏﯿﺮ ﻣﺸﺒﻌﺔ‬.2 ●

 2. Are stable unsaturated compounds. .‫ وﻏﯿﺮ ﻗﺎﺑﻠﺔ ﻟﻼﻣﺘﺰاج ﺑﺎﻟﻤﺎء‬، ‫ ھﻲ ﺑﺸﻜﻞ ﻋﺎم ﻣﺮﻛﺒﺎت ﻏﯿﺮ ﻗﻄﺒﯿﺔ‬.3 ●

 3. Are generally non-polar compounds, and immiscible with water.

 4. Give a sooty yellow flame due to the high ratio of carbon to
.‫ أﻋﻂ ﻟﮭﺒﺎ أﺻﻔﺮ ﺳﺨﺎﻣﯿﺎ ﺑﺴﺒﺐ ارﺗﻔﺎع ﻧﺴﺒﺔ اﻟﻜﺮﺑﻮن إﻟﻰ اﻟﮭﯿﺪروﺟﯿﻦ‬.4
hydrogen. .(‫ ﻏﺎﻟﺒﺎ )وﻟﻜﻦ ﻟﯿﺲ ﺑﺎﻟﻀﺮورة داﺋﻤﺎ( ﻟﮭﺎ رواﺋﺢ ﻣﻤﯿﺰة )رواﺋﺢ‬.5 ●
.‫ ﺗﺘﻤﯿﺰ ﺑﻮﺟﻮد ﺣﻠﻘﺔ ﺑﻨﺰﯾﻦ واﺣﺪة أو أﻛﺜﺮ ﻓﻲ اﻟﺠﺰيء‬.6 ●

 5. Often (but not necessarily always) have distinctive aromas (odors).

 6. Are characterized by the presence of one or more benzene rings in the
molecule. .(‫ ھﻲ ﺟﺰﯾﺌﺎت دورﯾﺔ )ﺣﻠﻘﺔ ﻣﻦ اﻟﺬرات‬.7 ●

 7. Are cyclic molecules (a ring of atoms).

 8. Are planar (all atoms in the molecule lie in the same plane).
 9. The molecule is fully conjugated (p orbitals at every atom in the ring).
 10. The molecule has 4n+2 pi electrons (n= any whole, positive integer).
 Thus, aromaticity is a property of cyclic (chain-shaped), planar (flat)
structures with a ring of resonance (conjugated pi system inside the
15
ring) bonds that gives greater stability.
 .‫ اﻟﻤﺘﺮاﻓﻖ داﺧﻞ اﻟﺤﻠﻘﺔ( اﻟﺘﻲ ﺗﻌﻄﻲ اﺳﺘﻘﺮارا أﻛﺒﺮ‬pi ‫ ﻣﺴﺘﻮﯾﺔ )ﻣﺴﻄﺤﺔ( ﻣﻊ ﺣﻠﻘﺔ ﻣﻦ اﻟﺮﻧﯿﻦ )ﻧﻈﺎم‬، (‫ ﻓﺈن اﻟﺮواﺋﺢ ھﻲ ﺧﺎﺻﯿﺔ ﻟﻠﮭﯿﺎﻛﻞ اﻟﺪورﯾﺔ )ﻋﻠﻰ ﺷﻜﻞ ﺳﻠﺴﻠﺔ‬، ‫وﺑﺎﻟﺘﺎﻟﻲ‬

Nomenclature of heterocyclic compounds

1. Common names ‫اﻷﺳﻤﺎء اﻟﺸﺎﺋﻌﺔ‬

‫ﺗﻢ إﻋﻄﺎء أﺳﻤﺎء اﻟﻤﺮﻛﺒﺎت اﻟﻌﻀﻮﯾﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ‬
Names of the heterocyclic organic compounds were given :‫ﺑﻨﺎء ﻋﻠﻰ‬
‫● ﺣﺪوﺛﮭﺎ‬
‫● اﻟﺘﺤﻀﯿﺮ اﻷول‬
‫● اﻟﻤﺼﺪر‬
based on: ‫● ﺑﻌﺾ اﻟﺨﺼﺎﺋﺺ اﻟﻤﻤﯿﺰة‬

 their occurrence

 first preparation

 source

 some characteristic properties

For example, the name of pyrrole was originated from the Greek
word for fiery red because of characteristic color.

 The disadvantages of this way of naming does not give any

structural information about the compound.
16
 Nomenclature of heterocyclic compounds

2. Systematic naming (IUPAC) (IUPAC) ‫ اﻟﺘﺴﻤﯿﺔ اﻟﻤﻨﮭﺠﯿﺔ‬.2

‫ﯾﺤﺪد ﻧﻈﺎم اﻟﺘﺴﻤﯿﺔ ھﺬا طﺒﯿﻌﺔ وﻣﻮﺿﻊ وﺣﺠﻢ اﻟﺤﻠﻘﺔ وﻋﺪد وأﻧﻮاع‬

This nomenclature system specifies the nature, position, ring size,

number, and types of heteroatoms present in any heterocyclic
compounds.

1 ‫ اﻟﺒﺎدﺋﺎت اﻟﺸﺎﺋﻌﺔ ﻣﻮﺿﺤﺔ ﻓﻲ اﻟﺠﺪول‬.‫ ﺗﺸﯿﺮ إﻟﻰ اﻟﺬرة ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ اﻟﻤﻮﺟﻮدة‬:‫اﻟﺒﺎدﺋﺔ‬
Prefix: Indicates the heteroatom present. The common prefixes
are shown in Table 1
‫ ﯾﺸﯿﺮ إﻟﻰ ﺣﺠﻢ اﻟﺤﻠﻘﺔ وﻛﺬﻟﻚ اﻟﺘﺸﺒﻊ وﻋﺪم اﻟﺘﺸﺒﻊ ﻓﻲ اﻟﺤﻠﻘﺔ‬:‫اﻟﺠﺬﻋﯿﺔ‬

Stem: Indicates the ring size as well as the saturation and

unsaturation in the ring.

S. No. Heteroatom Symbol Prefix

1 Oxygen O Oxa
2 Sulphur S Thia
3 Nitrogen N Aza

17
 Nomenclature of heterocyclic compounds
‫ أﻋﻀﺎء ﻋﻦ طﺮﯾﻖ اﻟﺠﻤﻊ ﺑﯿﻦ اﻟﺒﺎدﺋﺔ‬6 ‫ إﻟﻰ‬3 ‫ ﯾﺘﻢ ﺗﺴﻤﯿﺔ اﻟﺤﻠﻘﺎت أﺣﺎدﯾﺔ اﻟﺤﻠﻘﺔ اﻟﻤﻜﻮﻧﺔ ﻣﻦ‬، ‫ وﻓﻘﺎ ﻟﮭﺬا اﻟﻨﻈﺎم‬.IUPAC ‫اﻻﺳﻢ اﻟﻤﻨﮭﺠﻲ أو‬

 Systematic name or IUPAC. According to this system,

monocyclic 3 to 6-membered rings are named by combining
prefix in Table 1 with a suffix in Table 2, and “a” from end of
prefix has been omitted.

Unsaturated Saturated compounds

Ring size compounds
With N Without N With N Without N
3 -irine -irene -iridine -irane
4 -ete -ete -etidine -etane
5 -ole -ole -olidine -olane
6 -ine -in -ane -ane

18
Nomenclature of heterocyclic compounds

19
 Naming Rules
‫ﯾﺒﺪأ ﻣﻦ اﻟﺬرة ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ وﯾﺘﺤﺮك‬
 Starts from the heteroatom and moves ‫ﻓﻲ اﻻﺗﺠﺎه اﻟﺬي ﯾﺤﺼﻞ ﻋﻠﯿﮫ اﻟﺒﺪﯾﻞ‬
:‫ ﻋﻠﻰ ﺳﺒﯿﻞ اﻟﻤﺜﺎل‬.‫اﻟﻤﻮﻗﻊ اﻟﺴﻔﻠﻲ‬

in the direction where the substituent gets

lower location. For example:
‫ﻛﻠﺶ ﻛﻠﺶ ﻣﮭﻤﺎت ذﻧﻲ‬
:‫ ﺗﻜﻮن أوﻟﻮﯾﺔ اﻟﺬرات ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ ﻛﻤﺎ ﯾﻠﻲ‬، ‫ﺑﺎﻟﻨﺴﺒﺔ ﻟﻠﻤﺮﻛﺒﺎت أﺣﺎدﯾﺔ اﻟﺤﻠﻘﺔ اﻟﺘﻲ ﺗﺤﺘﻮي ﻋﻠﻰ أﻛﺜﺮ ﻣﻦ ذرة ﻏﯿﺮ ﻣﺘﺠﺎﻧﺴﺔ‬

 For monocyclic compounds having more than one heteroatom, the

priority of the heteroatoms is as follows:
1. If the group number of the heteroatoms are different, the atom
of the higher group number gets higher preference, for example,
O>N
2. If the group number of the heteroatoms are same, then the
lighter atom is preferred, for example, O (atomic mass 16) > S
(atomic mass 32)
‫ ﻓﺈن ذرة رﻗﻢ اﻟﻤﺠﻤﻮﻋﺔ‬، ‫ إذا ﻛﺎن رﻗﻢ ﻣﺠﻤﻮﻋﺔ اﻟﺬرات ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ ﻣﺨﺘﻠﻔﺎ‬.1

20
 Naming Rules
Heterocyclic compounds Containing more than one

Two or more similar atoms are indicated by prefixes di-, tri-,

etc. placed before the name and after the number of position.
‫ﻣﺮﻛﺒﺎت ﺣﻠﻘﯿﺔ ﻏﯿﺮ ﻣﺘﺠﺎﻧﺴﺔ ﺗﺤﺘﻮي ﻋﻠﻰ أﻛﺜﺮ ﻣﻦ واﺣﺪة‬
.‫ اﻟﻤﻮﺿﻮﻋﺔ ﻗﺒﻞ اﻻﺳﻢ وﺑﻌﺪ رﻗﻢ اﻟﻤﻮﺿﻊ‬.‫ إﻟﺦ‬، -di- ، tri ‫ﯾﺸﺎر إﻟﻰ ذرﺗﯿﻦ ﻣﺘﺸﺎﺑﮭﺘﯿﻦ أو أﻛﺜﺮ ﻣﻦ ﺧﻼل اﻟﺒﺎدﺋﺎت‬

1,2,4-Triazolidine
1,4-Dithiin
Two or more different hetero atoms named by combing the prefixes
in Table 1 with suffix in Table 2 in order of O, S and N.
‫ﺗﻢ ﺗﺴﻤﯿﺔ ذرﺗﯿﻦ ﻣﺨﺘﻠﻔﺘﯿﻦ أو أﻛﺜﺮ ﻣﻦ اﻟﺬرات ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ ﻋﻦ‬
2 ‫ ﻣﻊ اﻟﻼﺣﻘﺔ ﻓﻲ اﻟﺠﺪول‬1 ‫طﺮﯾﻖ ﺗﻤﺸﯿﻂ اﻟﺒﺎدﺋﺎت ﻓﻲ اﻟﺠﺪول‬
.N ‫ و‬S ‫ و‬O ‫ﺑﺎﻟﺘﺮﺗﯿﺐ‬

1,4-Oxazine
Oxaziridine
21
 Occurrence in Nature
، ‫ ﻋﻠﻰ ﺳﺒﯿﻞ اﻟﻤﺜﺎل‬، ‫ وﺗﺸﺎرك ﺑﻨﺸﺎط ﻓﻲ ﻋﻠﻢ اﻷﺣﯿﺎء‬، ‫ﺗﺤﺪث اﻟﻌﺪﯾﺪ ﻣﻦ اﻟﻤﺮﻛﺒﺎت اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ ﺑﺸﻜﻞ طﺒﯿﻌﻲ‬

 Many heterocyclic compounds occur naturally, and are

actively involved in biology, e.g.,
.(‫اﻷﺣﻤﺎض اﻟﻨﻮوﯾﺔ )ﻗﻮاﻋﺪ اﻟﺒﯿﻮرﯾﻦ واﻟﺒﯿﺮﯾﻤﯿﺪﯾﻦ‬
 Nucleic acids (purine and pyrimidine bases).
.(C ‫ وﺣﻤﺾ اﻷﺳﻜﻮرﺑﯿﻚ‬، B6 ‫ اﻟﺒﯿﺮﯾﺪوﻛﺴﯿﻦ‬، B3 ‫ اﻟﻨﯿﻜﻮﺗﯿﻨﺎﻣﯿﺪ‬، B2 ‫ اﻟﺮﯾﺒﻮﻓﻼﻓﯿﻦ‬، B1 ‫● اﻟﻔﯿﺘﺎﻣﯿﻨﺎت )اﻟﺜﯿﺎﻣﯿﻦ‬

 Vitamins (Thiamine B1, Riboflavin B2, Nicotinamide B3,

Pyridoxine B6, and Ascorbic acid C).
‫● اﻟﮭﯿﻢ واﻟﻜﻠﻮروﻓﯿﻞ واﻟﺒﻨﺴﻠﯿﻦ واﻟﺴﯿﻔﺎﻟﻮﺳﺒﻮرﯾﻨﺎت واﻟﻤﺎﻛﺮوﻟﯿﺪ وﻣﺎ إﻟﻰ ذﻟﻚ‬

 Heme and chlorophyll, penicillins, cephalosporins,

macrolides etc.
‫ﺗﻌﺪ دراﺳﺔ اﻟﻜﯿﻤﯿﺎء اﻟﺤﻠﻘﯿﺔ ﻏﯿﺮ اﻟﻤﺘﺠﺎﻧﺴﺔ ﻣﺠﺎﻻ واﺳﻌﺎ وﻣﺘﺰاﯾﺪا ﻟﻠﻜﯿﻤﯿﺎء ﺑﺴﺒﺐ ﺗﻄﺒﯿﻘﺎﺗﮭﺎ ﻓﻲ اﻟﻄﺐ واﻟﺼﯿﺪﻟﺔ‬

The study of heterocyclic chemistry is a vast and expanding

area of chemistry because of their applications in medicine,
pharmacy, agriculture, photodiodes and other fields.

22
 Medical Uses of Heterocyclic compounds
‫( اﻟﻤﻀﺎدات اﻟﺤﯿﻮﯾﺔ‬1
.‫ ﯾﻤﻜﻦ ﻟﻸدوﯾﺔ ﺗﺪﻣﯿﺮ )ﻗﺘﻞ( اﻟﺒﻜﺘﯿﺮﯾﺎ أو ﻣﻨﻊ ﺗﻜﺎﺛﺮھﺎ‬، (‫ )اﻟﺤﯿﺎة‬bios ‫ﯾﺄﺗﻲ ﻣﻦ اﻟﯿﻮﻧﺎﻧﯿﺔ اﻟﻤﻀﺎدة )ﺿﺪ( و‬
(1) Antibiotics !-Lactam ‫اﻟﻤﻀﺎدات اﻟﺤﯿﻮﯾﺔ‬
‫اﻟﺘﻲ ﺗﺤﺘﻮي ﻋﻠﻰ ﻣﺠﻤﻮﻋﺔ أزﯾﺘﺪﯾﻦ‬

comes from Greek anti (against) and bios (life), are drugs can
destroy (kill) bacteria or prevent their reproduction.
 -Lactam antibiotics
Which contain the azetidine group
(A) Penicillin analogous ‫ﻓﯿﻨﻮل‬
‫بنزين‬

0‫ النوع‬+‫هنا متشابهه بك‬

‫ﻛﯿﻒ ﺗﻔﺮق ﺑﯿﻨﮭﻤﺎ ﺑﺎﻟﻨﻈﺮ إﻟﻰ اﻟﺘﺮﻛﯿﺐ؟‬

C₆H₅-) ‫• إذا ﻛﺎﻧﺖ اﻟﺴﻠﺴﻠﺔ اﻟﺠﺎﻧﺒﯿﺔ ﻣﺠﻤﻮﻋﺔ ﺑﻨﺰﯾﻞ‬

Penicillin G ‫( → ھﺬا‬-CH₂
‫• إذا ﻛﺎﻧﺖ اﻟﺴﻠﺴﻠﺔ اﻟﺠﺎﻧﺒﯿﺔ ﻣﺠﻤﻮﻋﺔ ﻓﯿﻨﻮﻛﺴﻲ ﻣﯿﺜﯿﻞ‬ Penicillin G Penicillin V
Penicillin V ‫( → ھﺬا‬-C₆H₅-O-CH₂)

Another examples, Nafcillin, Cloxacillin, Amoxicillin

23
 Medical Uses of Heterocyclic compounds

(B) Cephalosporins

Drug R1 R2
Cefradine -CH3 NH2

Ceftrizoxime -H

Ceftriaxone

24
Medical Uses of Heterocyclic compounds
(C) Other -Lactams

Ertapenem

Clavulanic acid: Augmentin drug

(amoxicillin and clavulanic acid)

25
 Medical Uses of Heterocyclic compounds
‫ اﻟﻤﻀﺎدات اﻟﺤﯿﻮﯾﺔ ﻣﺎﻛﺮوﻟﯿﺪ‬.2

(2) Macrolide antibiotics

.(‫اﻷدوﯾﺔ اﻟﻜﺒﯿﺮة اﻟﺘﻲ ﺗﺤﺘﻮي ﻋﻠﻰ ﺣﻠﻘﺔ اﻟﻼﻛﺘﻮن اﻟﺤﻠﻘﯿﺔ اﻟﻜﺒﯿﺮة )ﺣﻠﻘﺔ اﻟﻤﺎﻛﺮوﻟﯿﺪ‬
- 16 ‫ و‬، (‫ )أزﯾﺜﺮوﻣﺎﯾﺴﯿﻦ‬- 15 ‫ و‬، (‫ )إرﯾﺜﺮوﻣﯿﺴﯿﻦ‬- 14 ‫ﻋﺎدة ﻣﺎ ﺗﻜﻮن ﺣﻠﻘﺎت اﻟﻼﻛﺘﻮن‬
(‫ وﺗﺴﺘﺨﺪم ﺑﺸﻜﻞ رﺋﯿﺴﻲ ﻓﻲ اﻟﻄﺐ اﻟﺒﯿﻄﺮي‬، ‫ﻋﻀﻮا )ﺗﺎﯾﻠﻮﺳﯿﻦ أ وﺟﻮﺳﺎﻣﯿﺴﯿﻦ‬
Large drugs containing macrocyclic lactone ring (macrolide ring).
The lactone rings are usually 14 - (Erythromycin), 15 - (Azithromycin),
and 16 - membered (Tylosin A and Josamycin, mainly used in Veterinary).
H 3C

N
H3C CH3

H3C
OH OH

H3C CH3 N CH3

OH
HO
O CH3
H3C O
O

CH3
CH3
O O
O

CH3
CH3
O
OH
CH3

Erythromycin Azithromycin
26
 Medical Uses of Heterocyclic compounds
(3) Quinolone antibiotics ‫( اﻟﻤﻀﺎدات اﻟﺤﯿﻮﯾﺔ اﻟﻜﯿﻨﻮﻟﻮن‬3

Nalidixic acid is first generation of quinolone used in 1962

for treatment of urinary tract infections (UTI) in human
CH3

‫ﻛﯿﻒ ﺗﻔﺮق ﺑﯿﻦ اﻟﺘﺮاﻛﯿﺐ اﻟﻜﯿﻤﯿﺎﺋﯿﺔ؟‬

H3C N N

quinolone O OH

Nalidixic acid

Ciprofloxacin Moxifloxacin 27
 Medical Uses of Heterocyclic compounds
‫اﻟﻤﻀﺎدات اﻟﺤﯿﻮﯾﺔ اﻟﺴﻠﻔﻮﻧﺎﻣﯿﺪ‬
(4) Sulfonamide antibiotics :‫ اﻣﺜﻠﮫ‬.‫ ﯾﺴﻤﻰ أدوﯾﺔ اﻟﺴﻠﻔﺎ‬، p-aminobenzoic ‫ﯾﺤﺘﻮي ﻋﻠﻰ ﺳﻠﻔﻮﻧﺎﻣﯿﺪ‬

Containing p-aminobenzoic sulfonamide, called sulfa

drugs. Examples: ‫ركب‬$‫اسم ا‬

‫اذا ضفنا هنا‬

Name of drug R Name of heterocyclic ring

Pyrimidine ‫ﻣﮭﻤﺎت‬
Sulfadiazine

Sulfamethazine Methazine

Sulfamethoxazole Methoxazole

28
 Medical Uses of Heterocyclic compounds
(2) Antiviral Drugs
Treatment viral infections, for example, Ritonavir is antiretroviral drug used to
treat HIV (Human Immunodeficiency virus) and AIDS (Acquired
Immunodeficiency Syndrome). Thiazole ring
‫( اﻷدوﯾﺔ اﻟﻤﻀﺎدة ﻟﻠﻔﯿﺮوﺳﺎت‬2
‫ رﯾﺘﻮﻧﺎﻓﯿﺮ ھﻮ دواء ﻣﻀﺎد‬، ‫ ﻋﻠﻰ ﺳﺒﯿﻞ اﻟﻤﺜﺎل‬، ‫ﻋﻼج اﻻﻟﺘﮭﺎﺑﺎت اﻟﻔﯿﺮوﺳﯿﺔ‬
‫ﻟﻠﻔﯿﺮوﺳﺎت اﻟﻘﮭﻘﺮﯾﺔ ﯾﺴﺘﺨﺪم ﻟﻌﻼج ﻓﯿﺮوس ﻧﻘﺺ اﻟﻤﻨﺎﻋﺔ اﻟﺒﺸﺮﯾﺔ‬
‫)ﻓﯿﺮوس ﻧﻘﺺ اﻟﻤﻨﺎﻋﺔ اﻟﺒﺸﺮﯾﺔ( واﻹﯾﺪز )ﻣﺘﻼزﻣﺔ ﻧﻘﺺ اﻟﻤﻨﺎﻋﺔ‬

Ritonavir

Another example: Nelfinavir 29

 Medical Uses of Heterocyclic compounds
(3) Antifungal Drugs
Treatment fungal infections. The azole antifungal include two
broad classes, Triazoles and Imidazoles ‫( اﻷدوﯾﺔ اﻟﻤﻀﺎدة ﻟﻠﻔﻄﺮﯾﺎت‬3

Triazole drugs

Fluconazole Voriconazole
‫ ﻧﯿﺘﺮوﺟﯿﻦ‬3 ‫ﺗﺤﺘﻮي ؏ـﻠـَۍ ﺣﻠﻘﺘﯿﻦ ﺧﻤﺎﺳﯿﮫ ﻛﻞ ﺣﻠﻘﮫ ﺑﯿﮭﺎ‬

Ravuconazole 30
 ‫‪Medical Uses of Heterocyclic compounds‬‬

‫)‪(4) Anticonvulsants Drugs (antiepileptic‬‬

‫‪ (4‬اﻷدوﯾﺔ اﻟﻤﻀﺎدة ﻟﻼﺧﺘﻼج )ﻣﻀﺎدات اﻟﺼﺮع(‬
‫ﻋﻼج ﻧﻮﺑﺎت اﻟﺼﺮع‬
‫‪Treatment epileptic seizures.‬‬

‫‪Phenobarbital‬‬ ‫‪Oxcarbaepine‬‬ ‫‪Troxidone‬‬

‫)‪(diazane ring‬‬ ‫)‪(azepine ring‬‬ ‫)‪(oxazolidine ring‬‬
‫ﻛﯿﻒ ﺗﻤﯿﺰ ﺑﯿﻦ اﻷدوﯾﺔ ﺑﻨﺎ ًء ﻋﻠﻰ ﺗﺮﻛﯿﺒﮭﺎ؟‬
‫ﻓﯿﻨﻮﺑﺎرﺑﯿﺘﺎل )ﺣﻠﻘﺔ دﯾﺎزان(‬ ‫• ﺣﻠﻘﺔ ‪ → Azepine‬ﻣﻮﺟﻮدة ﻓﻲ ‪) Oxcarbazepine‬ﺣﻠﻘﺔ‬
‫ﺳﺒﺎﻋﯿﺔ ﺑﮭﺎ ﻧﯿﺘﺮوﺟﯿﻦ(‪.‬‬
‫)‪ azepin‬ﺣﻠﻘﺔ( ‪Oxcarbaepine‬‬
‫• ﺣﻠﻘﺔ ‪ → Oxazolidine‬ﻣﻮﺟﻮدة ﻓﻲ ‪Trimethadione‬‬
‫ﺗﺮوﻛﺴﯿﺪون )ﺣﻠﻘﺔ أوﻛﺴﺎزوﻟﯿﺪﯾﻦ(‬ ‫)‪) (Troxidone‬ﺣﻠﻘﺔ ﺧﻤﺎﺳﯿﺔ ﺑﮭﺎ أﻛﺴﺠﯿﻦ وﻧﯿﺘﺮوﺟﯿﻦ(‪.‬‬
‫اﻟﻔﯿﻨﺴﻮﻛﺴﯿﻤﯿﺪ )ﺣﻠﻘﺔ اﻟﺴﻜﺴﯿﻨﯿﻤﯿﺪ(‬
‫• ﺣﻠﻘﺔ ‪ → Succinimide‬ﻣﻮﺟﻮدة ﻓﻲ ‪Phensuximide‬‬
‫)ﺣﻠﻘﺔ ﺧﻤﺎﺳﯿﺔ ﺑﮭﺎ ﻣﺠﻤﻮﻋﺘﺎ ﻛﺮﺑﻮﻧﯿﻞ(‪.‬‬
‫ﻻ ﯾﺤﺘﻮي ﻋﻠﻰ أي ﻣﻦ ھﺬه اﻟﺤﻠﻘﺎت‪ ،‬ﻟﻜﻨﮫ ‪• Phenobarbital‬‬
‫‪Phensuximide‬‬ ‫ﯾﻨﺘﻤﻲ إﻟﻰ اﻟﺒﺎرﺑﯿﺘﻮرات‬
‫)‪(succinimide ring‬‬ ‫‪31‬‬
 ‫‪Medical Uses of Heterocyclic compounds‬‬

‫‪(5) Antipyretic and Non‐steroidal anti‐inflammatory Drugs‬‬

‫‪ (5‬اﻷدوﯾﺔ اﻟﺨﺎﻓﻀﺔ ﻟﻠﺤﺮارة وﻏﯿﺮ اﻟﺴﺘﯿﺮوﯾﺪﯾﺔ اﻟﻤﻀﺎدة ﻟﻼﻟﺘﮭﺎﺑﺎت‬
‫‪Pyrazolone derivatives‬‬ ‫ﻣﺸﺘﻘﺎت ﺑﯿﺮازوﻟﻮن‬

‫ھﺬا اﻟﻌﻼج اﻧﻘﺮض‬

‫‪Phenazone‬‬ ‫‪Metamizaole‬‬ ‫‪Aminophenazone‬‬

‫ﻓﯿﻨﺎزون‬ ‫ﻣﯿﺘﺎﻣﯿﺰاول‬ ‫أﻣﯿﻨﻮﻓﯿﻨﺎزون‬
‫• ﺟﻤﯿﻌﮭﺎ ﺗﺤﺘﻮي ﻋﻠﻰ ﻧﻮاة اﻟﺒﯿﺮازوﻟﻮن )‪ ،(Pyrazolone Ring‬وﻟﻜﻦ ﺗﺨﺘﻠﻒ ﻓﻲ اﻟﻤﺠﻤﻮﻋﺎت اﻟﺠﺎﻧﺒﯿﺔ )‪ (R groups‬اﻟﺘﻲ ﺗﺆﺛﺮ ﻋﻠﻰ ﻗﻮة‬
‫اﻟﺘﺄﺛﯿﺮ‪ ،‬ﻣﺪة اﻟﻔﻌﺎﻟﯿﺔ‪ ،‬وآﺛﺎره اﻟﺠﺎﻧﺒﯿﺔ‪.‬‬

‫ﺗﺠﻌﻠﮫ أﻛﺜﺮ ذوﺑﺎﻧًﺎ وﺗﺄﺛﯿ ًﺮا ﻛﺨﺎﻓﺾ ﺣﺮارة )‪ (-SO₂‬ﯾﺤﺘﻮي ﻋﻠﻰ ﻣﺠﻤﻮﻋﺔ ﺳﻠﻔﻮﻧﯿﻞ ‪• Metamizole‬‬
‫‪32‬‬
 Medical Uses of Heterocyclic compounds
(6) Cytostatic Drugs
‫اﻟﻌﻮاﻣﻞ اﻟﻤﻀﺎدة ﻟﻸورام اﻟﻤﺴﺘﺨﺪﻣﺔ ﻟﻌﻼج أﺷﻜﺎل ﻣﺨﺘﻠﻔﺔ ﻣﻦ‬
Antineoplastic agents used to treat various forms of cancer.

Fluorouracil Cladribine
(pyrimidine ring) (purine ring)
(‫ﻓﻠﻮروﯾﻮراﺳﯿﻞ )ﺣﻠﻘﺔ ﺑﯿﺮﯾﻤﯿﺪﯾﻦ‬ (‫ﻛﻼدرﯾﺒﯿﻦ )ﺣﻠﻘﺔ اﻟﺒﯿﻮرﯾﻦ‬
‫ﻛﯿﻒ ﻧﻔﺮق ﺑﯿﻨﮭﻤﺎ؟‬

Methotrexate (antifolate) ‫ﻣﯿﺜﻮﺗﺮﯾﻜﺴﺎت )ﻣﻀﺎد ﺣﻤﺾ‬

(pteridine ring) (‫اﻟﻔﻮﻟﯿﻚ( )ﺣﻠﻘﺔ ﺑﺘﺮﯾﺪﯾﻦ‬ 33
 Medical Uses of Heterocyclic compounds
(7) Anti-Histamine Drugs
‫ اﻷدوﯾﺔ اﻟﻤﻀﺎدة ﻟﻠﮭﯿﺴﺘﺎﻣﯿﻦ‬.7
‫ ﺗﻌﻤﻞ ﻛﻤﻀﺎدات اﻟﮭﯿﺴﺘﺎﻣﯿﻦ‬HCS ‫ھﻨﺎك أﻧﻮاع ﻣﺨﺘﻠﻔﺔ ﻣﻦ‬
There are different H.Cs. act as antihistamines
‫ﻛﯿﻒ ﻧﻔﺮق ﺑﯿﻨﮭﻤﺎ ﺑﻨﺎ ًء ﻋﻠﻰ اﻟﺘﺮﻛﯿﺐ؟‬

Promethazine Hydroxyzine
Phenothiazine derivatives Piperazine analogues
‫ﻣﺸﺘﻘﺎت ﺑﺮوﻣﯿﺜﺎزﯾﻦ ﻓﯿﻨﻮﺛﯿﺎزﯾﻦ‬ ‫ھﯿﺪروﻛﺴﯿﺰﯾﻦ‬
‫ﻧﻈﺎﺋﺮ ﺑﯿﺒﯿﺮازﯾﻦ‬

34
 References
1. Organic Chemistry by Robert T. Morrison and Robert N.
Boyed, latest edition.
2. Organic Chemistry by J. McMurry, latest ed., Thomason
learning, CA, USA.
3. An introduction to the chemistry of heterocyclic
compound by Acheson, R. M. latest ed.

Good Luck

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3/12/2025 Dr. Dhiaaddin Al-Saadi
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3/12/2025 Dr. Dhiaaddin Al-Saadi