Organic chemistry III

Heterocyclic System
Lec 1 & 2

1 College of Pharmacy /AlKitab University by

Nohad A AlOmari
1-To identify types of heterocyclic compounds
2- To know sources of heterocyclic
3-To know syntheses of heterocyclic compounds
compounds
4-To understand chemical reactions of
heterocyclic Compounds
5- occurrence in nature and in medicinal compounds.

2 College of Pharmacy /AlKitab University by

‫‪ 28‬أيار‪19 ،‬‬
 Heterocyclic system:
1. Classes of Heterocyclic system
2. Genearl structure; Occurrences in nature
and in medicinal products

3 College of Pharmacy /AlKitab University by

‫‪ 28‬أيار‪19 ،‬‬
 Heterocyclic System
Any of a class of organic compounds whose molecules contain one
or more rings of atoms with at least one atom (the heteroatom)
being an element other than carbon, most frequently oxygen,
nitrogen, or sulfur.
Heterocyclic compounds include many of the biochemical material
essential to life. For example, nucleic acids, the chemical
substances that carry the genetic information controlling
inheritance, consist of long chains of heterocyclic units held
together. Many naturally pigments, vitamins, and
occurring
antibiotics are heterocyclic compounds.
4 College of Pharmacy /AlKitab University
 Heterocyclic derivatives and classification
Heterocyclic derivatives as a group, can be divided into two broad areas:
aromatic and non-aromatic. (note : aromatic system must have 4n+2 π-electron)

1) the 1, five-membered rings are shown below, the derivative furan 1 is aromatic,
while tetrahydrofuran (2), dihydrofuran-2-one (3) are not aromatic, Why?.

2) The six-membered rings below, pyridine is aromatic (5), while piperidine (6),
piperidin-2-one (7) are not aromatic, why?
Most heterocycles have the same chemistry as their open-chain counterparts 
particularly when the ring is unsaturated.

College of Pharmacy /AlKitab University by

5 19 ،‫ أيار‬28
Nohad A AlOmari
In general :
heterocyclic is the largest and most varied family of organic compounds,
heterocyclic system can be 3, 4, 5, 6, 7 membered rings
in addition to a fused rings (two rings
joined at two adjacent atoms)
Stems for the 3 to 6 heterocyclics:

S no: Ring size Unsaturation Saturation

1 3 membered -irene -irane

2 4 membered -ete -etane

3 5 membered -ole -olane

4 6 membered -ine
(1)O,S, (2)N,Si, -ine -ane
(3)B,P, -inine -inane
-inane
 Rules that have to be considered while giving names to the
heterocyclic compounds:

The names of the monocyclic compounds are derived by a prefix

indicating the nature of heteroatoms present and introducing or omitting
the “a” where necessary.

Eg :
2
3 2

1 HN 3 4 O1
Aziridine oxetan

When two are more of the same heteroatoms are present, the prefixes
“di,tri”etc. are used.

4 O
3

5 2
1
O
1,3-dioxolane
If the heteroatoms are different they are named in the order of “O, S, N, P, Si”
etc. by combining the prefixes with the ending in the order of preference.
Eg:
5
6 4 3
4 N
5
3 N 2
S O
1 1
2N
thiazine 1,2,3-Oxadiazole
-The state of hydrogenation is indicated in the suffix or by the prefixes dihydro,
tetrahydro etc or by prefixing the name of the parent unsaturated compound with
the symbol ”H” preceeded by a number indicating the position of saturation.
Eg:
5
S
4 6

3 S 1
N2
H
2H,6H-1,5,2-dithiazine

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10 19 ،‫ أيار‬28
Nohad A AlOmari
In a monocyclic compound containing only one heteroatom numbering starts at this
atom. The ring is numbered to give the substituents or other heteroatoms the lowest
number possible.
N
Eg:

quinoline
or
2,3-benzopyridine

NOMENCLATURE OF FUSED HETEROCYCLIC COMPOUNDS:

. When the parent compound has been chosen, its name is prefixed by the name
of the fused ring attached (ex: benz (0),napth(o)) also the parent compound
chosen is the component containing the largest number of rings and has a simple
name.
Eg:
7
1O
6
2
5
3
4
College of Pharmacy /AlKitab University by
11 19 ،‫ أيار‬28
Nohad A AlOmari
 benzofuran

College of Pharmacy /AlKitab University by

12 19 ،‫ أيار‬28
Nohad A AlOmari
. Numbering is then carried out in a clockwise direction starting with the
uppermost ring farthest to right and omitting atoms at right junctions.
6
Ex
N 5
7 4
8 3
N N

10 1 2
9 triazaphenanthrene
-In a heterocyclic ring numbering preferably commence at a saturated
rather than at an unsaturated heteroatom

H
N
N
CH3

C 2H 5
3-ethyl-5methyl pyrazole
Bicyclic bridged structures are quite common. The nomenclature of such a
structure consists of the prefix bicycle, followed in square brackets the number of
carbon atoms separating the bridge heads by the three possible routes in
descending numerical order.
Eg:

2
O
1 3
8
H

7 4
H
O 5
6

3,6-dioxabicyclo[3.1.0]octane
Occurrence in nature

Heterocyclic compounds include many of the biochemical material essential to

life. For example, nucleic acids, the chemical substances that carry the genetic
information controlling inheritance, consist of long chains of heterocyclic units
held together. Many naturally occurring pigments, vitamins, and antibiotics are
heterocyclic compounds.

Ergot, a fungal disease of cereal grasses,

is caused by the fungus Claviceps
purpurea, which produces indole
alkaloids

Nohad A AlOmari
14 College of Pharmacy /AlKitab University by
19 ،‫ أيار‬28

Nohad A AlOmari
Occurance in pharmaceutical Products
Activity 1
in the following slid a top 200 pharmaceutical products by US prescription in 2012
http://cbc.arizona.edu/njardarson/group/top-pharmaceuticals-poster
open the link, choose one product, find the kinds of hetero rings system and write a short note
on its used (2-5 lines only) see the example bellow

15 College of Pharmacy /AlKitab University by

‫‪ 28‬أيار‪19 ،‬‬
 College of Pharmacy /AlKitab University by
16 19 ،‫ أيار‬28
Nohad A AlOmari