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Hetercyclic Chem - 4th Sem Weak - 1

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38 views14 pages

Hetercyclic Chem - 4th Sem Weak - 1

Uploaded by

irfanshah
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© © All Rights Reserved
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Prepared by:Irfan Shah

Chemistry teacher
QUSIT Peshawar
Nomenclature of Heterocyclic
Compounds

What are hetercyclic compounds


Cyclic compounds containing at
least one atom other than carbon
in the cycle called heterocyclic
compounds.
e.g. Thirane Aziridine

oxirane
The IUPAC rules allow three nomenclatures.

I. The Hantzsch-Widman Nomenclature.


II. Common Names
III. The Replacement Nomenclature
I. Hantzsch-Widman Nomenclature

The Hantzsch-Widman nomenclature is based on the type (Z) of the


heteroatom; the ring size (n) and nature of the ring, whether it is
saturated or unsaturated .
This system of nomenclature applies to monocyclic three-to-ten-
membered ring heterocycles.
Example

Where n= 1,2,3,…..
I. Type of the heteroatom (Z)

Thetype of heteroatom is indicated by a prefix as shown below for


common hetreroatoms:

Hetreroatom Prefix

O Oxa

N Aza

S Thia

P Phospha
II. Nomencalture based on Ring size (n)

The ring size is indicated by a suffix according to Table 1 below.


Some of the syllables are derived from Latin numerals, namely ir
from tri, et from tetra, ep from hepta, oc from octa, on from nona,
ec from deca.

Table 1: Stems to indicate the ring size of heterocycles

Ring size Suffix Ring size Suffix


3 ir 7 ep
4 et 8 oc
5 ol 9 on
6 in 10 ec
The endings indicate the size and degree of
unsaturation of the ring.

Table II: Stems to indicate the ring size and degree of


unsaturation of heterocycles
Ring size Saturated Unsaturated Saturated (With Nitrogen)
3 -irane -irine -iridine
4 -etane -ete -etidine
5 -olane -ole -olidine
6 -inane -ine
7 -epane -epine
8 -ocane -ocine
9 -onane -onine
10 -ecane -ecine
Exampl
es

Oxa+irane= Oxirane Thia+irane= Thiirane Aza+iridine= Aziridine

Oxa+etane=Oxetan Thia+etane=Thietan Aza+etidine=Azetidine


e e

Oxa+olane= Oxolane Thia+olane= Thiolane Aza+olidine= Azolidine


Azine
Azinane
Pyridin
e
In case of substituents, the heteroatom is designated number 1,
and the substituents around the chain are numbered so as to
have the lowest number for the substituents.
Rings With More Than One Heteroatom

Two or more similar atoms contained in a ring are indicated by


the prefixes ‘di-’, ‘tri’, etc.

1,3,5-Triazine

If more than one hetero atom occur in the ring, then the
heterocycle is named by combining the appropriate
prefixes with the ending in Table I in order of their
preference, O > S > N.
1,3-
Oxaziridine Thiazole
(Thiazole)

1,4-Oxazine 3-chloro-5-methyl-1,2,4-oxadiazole
II. Common Names
There are a large number of important
ring systems which are named widely
known with their non-systematic or
common names.
H
O
N

Furan Pyrrole
N
O O
Isoquinoline Coumarin

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