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Fused - Heterocycles Nomenclature

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NOMENCLATURE

OF FUSED RING
HETEROCYCLES

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Hantzsch-Widman
Nomenclature Fused Ring
Heterocycles
• Fused heterocycles are systems constructed by combining two or more rings.
• The rings are fused if they are linked in such a way that each ring has one common
bond (fusion bond) to each other.
• Moreover, each of the fused ring units should contain a maximum number of non-
cumulative double bonds.
• There are two broad types of fused heterocycles.
• 1. aromatic carbocycle linked to a heterocycle .
• 2. heterocycle linked to another heterocycle.

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Hantzsch-Widman Nomenclature
Rules for Naming Fused Heterocycles
• Many of these fused heterocycles occur naturally in
plant and animal systems, and some are used
commercially.
• Due to their traditional uses, some of these heterocycles
have trivial names that reflect these uses, but also have
IUPAC names that reflect their structure.
• The general format for the name of a fused heterocycle
involving a carbocycle fused to a heterocycle is:

• To generate this name, it is necessary to identify the


fused or attached ring and the base ring that will be the
parent ring that will provide the suffix of the molecule. 3
Hantzsch-Widman Nomenclature
Rules for Naming Fused Heterocycles
• To derive the name of the fused heterocycle, the
attached component is added as a prefix to the name of
the base component.
• The prefix in such names is generated by replacing the
terminal ‘e’ in the name of the attached component by
‘o’, i.e. benzo, naphtho and so on.
• The prefixes for the common aromatic heterocycles are
listed below:
 Furan = furo
 Thiophene = thieno
 Pyridine = pyrido
 Pyrrole = pyrrolo
 Imidazole = imidazo
 Quinoline = quino 4
Hantzsch-Widman Nomenclature
Identifying the Fused Components
• To identify the fused components of a fused
heterocycle, dissect it along the fusion bond into its
component rings to set one as its base component and
the other will be designated as the attached component.

• Note that the base component is always a heterocyclic


system. The components are given their recognized
trivial names (if possible) else, systematic name is used.
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Hantzsch-Widman Nomenclature
Naming a Carbocycle Fused to
Heterocycle
• To name a fused heterocycle, derived from the fusion of
a carbocycle to a heterocycle:
i. Derive the parent name (written at the end) from the
name of the heterocyclic ring (base component).
ii. Generate the attached name (written first) from the
name of the attached benzene (i.e Benzo).
iii.The bond of fusion of the parent ring with the
attached benzene ring is indicated using alphabetical
letters (a, b, c etc) placed in square brackets between
the prefix and parent name.
iv.To determine the alphabet for the bond of fusion,
number the parent ring from the heteroatom to the
fusion bond such that side 1,2, takes letter (a), side 2,3
takes letter (b), side 3, 4 takes letter (c) etc. 6
Hantzsch-Widman Nomenclature
Worked Example: Indole
• To nomenclature of indole illustrated below shows how
fused heterocycles with a carbocycle fused to a
heterocycle are named:

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Hantzsch-Widman
Nomenclature Carbocycle
Fused to
• Following Heterocycle
a similar approach, verify that the
fused heterocycles below are named as follows:

• Note that when the fused heterocycles are partially


saturated or substituted, the total numbering of the
complete fused system is done to determine the
positions of saturations or substitutions.
• The numbering starts from the atom next to the fusion
point giving the heteroatom the least possible locant and
the fused bond is given the fusion number using letters
(a, b, c, etc). 8
Hantzsch-Widman Nomenclature
Heterocycle Fused to Another
Heterocycle
• The IUPAC nomenclature of such systems is based on:
i. The parent name (suffix) of the base component is
given by the higher priority heterocycle.
ii. The attached component is the ring name
of the lower priority ring and is used as
• Thethe prefix.
bond of fusion is indicated by numbers and an
appropriate letter enclosed in a square bracket and
placed immediately after the prefix.
• The numbers (positions of attachment) of the attached
component are placed in the sequence in which they are
attached to the base component.
• For substituted systems, the total numbering of the fused
heterocycle is in the usual way 1,2,3….based on the
principle of lowest possible numbering. 9
Hantzsch-Widman Nomenclature
Heterocycle Fused to Another
Heterocycle
• The general format for capturing the name of a fused
heterocycle combining a heterocycle fused to another
heterocycle is summarized below:
i. The parent or base name given by the higher priority
heterocycle is used as suffix.
ii. The fused ring name is the lower priority ring and is
used as prefix.

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Hantzsch-Widman Nomenclature
Rules for Fused Aromatic Heterocycles
1.If there is only one component that contain N in fused ring
then N containing ring will make base ring and will be in
suffix and other attached ring will be as prefix .

2. If nitrogen is absent, then the ring with higher priority


heteroatom(s) will be base component . (oxygen >
sulphur).

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Hantzsch-Widman Nomenclature
Rules for Fused Aromatic Heterocycles
3. If both ring have the same heteroatom, but unequal in
size , then largest size ring will make base product.

4. If rings of equal size with different number of


heteroatoms are present, then the ring with greater number
of heteroatoms of any kind is considered as a base
component.

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Hantzsch-Widman Nomenclature
Fused Heterocycles: Worked Example
5. Illustrated below is the process of naming a fused
heterocycle combining a heterocycle fused to another
heterocycle.

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Worked
Nomenclature of Fused Heterocycles
Examples
Note in these examples that the number for the obligatory
saturated carbon is determined by the numbering that gives
the two heteroatoms the lowest combination of location
numbers.

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Hantzsch-Widman Nomenclature
Fused Heterocycles with Polyheteroatoms
• For fused heterocycles containing a heterocycle with a
multiplicity of heteroatoms, the ring containing the
greatest number of heteroatoms or greatest varieties of
heteroatoms is the parent ring.

• The peripheral numbering of the total heterocyclic fused


molecule is by giving the lowest number to the higher
priority heteroatom especially when present just after
fusion. But, if the more prior heteroatom is not the
nearest to the fusion side the other nearest heteroatoms
after fusion must take the least possible numbering 15
regardless of priority.
Hantzsch-Widman Nomenclature
Fused Heterocycles with poly Heteroatoms

• For fused heterocycles containing a heterocycle with a


similar number and type of heteroatoms, the ring
containing the greater number of carbon atoms adjacent
to the bond of fusion is the parent ring.

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Heterocycles containing more then two ring
If the ring contain same heteroatom and more then two rings are present
,then choose the component contating the greter no of ring
Practice Questions
Nomenclature of Heterocycles
Provide the IUPAC names of the fused
following
heterocycles.

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