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presentation on,

HETEROCYCLIC CHEMISTRY

By-Mr.A.B.Jagnar

Amrutvahini Sheti & Shikshan Vikas Sanstha’s,

Amrutvahini Institute of Pharmacy,

Sangamner.
Organic chemistry
is the study of the structure, properties, composition, reactions, and
preparation of carbon-containing compounds, which include not only
hydrocarbons but also compounds with any number of other elements,
including hydrogen (most compounds contain at least one carbon–
hydrogen bond), nitrogen, oxygen, ...
Types of Organic Compounds
Aliphatic Compounds
Compounds which consist of open-chain of carbon atoms.
H3C - CH3
Ethane
CH3-CH2-CH3
Propane

Hydrocarbons: Compounds which contain only carbon and

hydrogen.
Saturated Compounds – A hydrocarbon is said to be saturated if
it contain only C – C single bonds.

H3C - CH3
Ethane

Unsaturated Compounds – A hydrocarbon is said to be

unsaturated
if it contains C=C or multiple bonds.
H2C = CH2
Ethene
Aromatic Compounds-
Benzene and all compounds that have structure and chemical
properties resembling benzene are called aromatic compounds.
BENZENE ANILINE
NH2

Each corner
represent
CH group
Alicyclic Compounds
Cyclic compounds which consist only of carbon
atoms are called alicyclic or carbocyclic compounds
Cyclopropane

Each corner represent -CH2 group

HETEROCYCLIC CHEMISTRY

 -Heterocycliccompounds are those compounds

which possess a heterocyclic or ring structure with
at least two different kinds of atoms (including
carbon atom) in the ring.

 When one or more of carbon atom

in carbocyclic compounds is replaced
with heteroatom (N, S or O).
 N
Carbon atom replaced by
‘N’
Pyridine
Benzene

Nomenclature and numbering-

To understand the nomenclature and numbering we first have
to learn some rules which govern the numbering of
heterocyclic comp:
A. simple heterocyclic ring containing one heteroatom-

1. The heteroatom in the numbering is counted as one and other

atoms are numbered either clockwise or anticlockwise direction.

2. If the substituent group is present then the numbering is given

in a such a way that the substituent should bear least possible
numbers.

3. If more than one substituent group are present in heterocyclic

ring then they should bear least possible numbers. The groups are
arranged in alphabetical order.

4. If the heterocyclic ring contains two or more different

heteroatoms, then the order of preference for position 1 is oxygen,
sulphur and then nitrogen and the other heteroatom are given
lowest possible number.
5. if the heterocyclic ring contains two or more nitrogen atom,
then saturated nitrogen(N-H) should bear no.1.
6. in certain fused ring compound the numbering not starts from heteroatoms
in phenothiazine- sulphur and
Eg. Isoquinoline – nitrogen bear 2nd no. nitrogen given no.5 &10 resp
.

in acridine -nitrogen bears 10 no

Purine-
.
1.The name of 5 membered heterocycle ring containing two double bonds ends with –
ole.
1

2.

In this type the terminal –e of –ole is replaced by pyrazoline-- five

membered heterocyclic ring containing 1 double bond.

3. If both double bond are saturated then –e replaced with –idine.

pyrazolidine- five membered

heterocyclic ring containing two
nitrogen & no double bond.
Six membered heterocycle containing 3 double bonds
generally ends with -ine

six membered ring containing 1 nitrogen at 1 position.

The name of a heterocycle ring can be obtained by using

prefix for heteroatom

Heteroatom Prefix
Nitrogen Aza/azo/Pyr
Sulphur Thia/thio
Oxygen Oxa
Thus,thiazole is 5 membered ring containing 2 double bonds and
two heteroatoms namely sulphur and nitrogen.
To give chemical name to a given structure of
drug-

1. Choose parent skeletal structure and number according to the

rules .

2. if the substituents are complicated then separate numbering

should be given to them.
The carbon atom (Except that of heterocycle) of the substituent
which is attached to the parent structure should given no.1

3. First write the names of substituents, prefixed with numbers in

alphabetical order. (Complicated substituents should be written in
bracket)
4. Finally write name of parent skeletal structure.
1,3,4-thiadiazole is choosen as parent ring
At C 2 acetamido group is present and at C 5 sulphamoyl group is
present..
Therefor chemical name can be written as

2-acetamido,5-sulphamoyl,1,3,4-thiadiazole.

WHILE DRAWING CHEMICAL STRUCTURE

FROM CHEMICAL NAME...
Draw parent structure first
Number accordibg to the rules
Write the group at specified positions
e.g.
2-acetamido,5-sulphamoyl,1,3,4-thiadiazole.
Note-If Nitrogen atom except of heterocycle of a parent structure
is substituted then the name is written as,
i. N-(Substituent name) when only one substituent

ii. N,N-(disubstituent name) when two same substituent

iii. N-(Substituent name) ,N-(substituent name), N-(substituent

name)when two different substituents present.

N,N-diethyl,pyridine-3-carboxamide.
1.pyrrole- five 2. pyrazole-- five 3. pyrazoline-- five 4. 5. imidazole- 31. cepham-
membered membered membered pyrazolidine- five membered
heterocyclic ring heterocyclic ring heterocyclic ring five membered heterocyclic
containing one containing two containing two heterocyclic ring containing
nitrogen at nitrogen at 1 & 2 nitrogen & 1 double ring containing two nitrogen at
position1. position. bond. two nitrogen & 1&3 position.
no double
bond. Eg.
Cephalexin.

eg.analgin .
eg. Tolmetin. eg. anti-pyrine. eg.
Metronidazole,
eg. Phenyl phenytoin
butazone.

11.furan-- five 7. Oxazole- - 8. Iso-oxazole- - 10.thiole/thiop 9. thiazole- - 19.Barbituric

membered five membered five membered hene - five five membered acid -
heterocyclic ring heterocyclic ring heterocyclic ring membered heterocyclic
containing one containing containing oxygen heterocyclic ring containing
oxygen atom at oxygen at postion at postion 1 & ring containing sulphur atom at
position1. 1 & nitrogen at 3. nitrogen at 2. one sulphur position1 &
atom at nitrogen at 3
position1. position.

eg.
Phenobarbiton
eg.sulphaisoxazole e
eg.furan,ranitidine eg. Bengazole.

eg.
eg.thiamine,sul
cephalothine
phathiazole.

13.pyridine- six 14. pyridazine- 15. pyrimidine -six 16.pyrazine- 17. piperidine- 18.
membered ring six membered membered ring six membered pyridine with piperazine-
containing 1 ring containing 2 containing 2 ring containing no bonding pyrazine with
nitrogen at 1 nitrogen at 1 &2 nitrogen at 1 &3 2 nitrogen at 1 no bonding.
position. position. position. &4 position.

. eg.
Pepthidine,glut
eg. ethimide.
Nikethamide,isoni eg.DEC.
eg.pyrimethamine, eg.
azide. eg. pyrazinamide
Sulphamethoxypy
ridazine
Organic groups-
n-propyl Cyno/nitrile Carbamoyloxy
phenyl Oxo/carbonyl n-methyl carbamoyl
benzyl Formyl benzoyl
amino Carboxyl/carboxy benzolyoxy
aniline Acetyl(ethanoyl) phenoxy
amidino Acetoxy phenoxymethyl
guanidine Propanoyloxy nitro
biguanidino Carbamoyl/ sulphonamide/sulphamoyl
carboxamide
p-amino benzene p-methoxy benzoyl
sulphonamide acetamido
International Union of Pure and Applied Chemistry
(IUPAC)
The systematic name of a compound derived from its
structural formula by applying IUPAC rules, is called as its
IUPAC Name.
Number of Name Structural formula
carbon
atoms
1 Methane CH4
2 Ethane CH3-CH3
3 Propane CH3-CH2-CH3
4 Butane CH3-CH2-CH2-CH3
5 Pentane CH3-CH2-CH2-CH2-CH3
6 Hexane CH3-CH2-CH2-CH2-CH2-CH3
7 Heptane CH3-CH2-CH2-CH2-CH2-CH2-CH3
8 Octane CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH3
9 Nonane CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3
1 Decane CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-
0 CH3
 Table: Names of Common Alkyl Groups

No of Parent Name Name of alkyl group

carbo alkane of
n alkyl
atom group
s
1 Methane Methyl CH3-
2 Ethane Ethyl CH3-CH2-
3 Propane Propyl CH3-CH2-CH2-
4 Butane Butyl CH3-CH2-CH2-CH2-
5 Pentane Pentyl CH3-CH2-CH2-CH2-CH2-
6 Hexane Hexyl CH3-CH2-CH2-CH2-CH2-CH2-
7 Heptane heptyl CH3-CH2-CH2-CH2-CH2-CH2-CH2-
8 Octane Octyl CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-
9 Nonane Nonyl CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-
CH2-
1 Decane Decyl CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-
0 CH2-CH2-
Functional Group Suffix used

Class Functional Group Suffix used

Carboxylic acid -COOH -oic acid
Sulphonic acid -SO3H -sulphonic acid
Ester -COO-R Alkyl -oate
Acid Halides -CO-X (X= Cl, Br, I, F) -oyl halide
Amide -CONH2 -amide
Nitrile -CN -Nitrile
Aldehyde -CHO -al
Ketone -CO- -one
Alcohol -OH -ol
Amines -NH2 -amine
Ethers -O- ether
Alkene -C=C- -ene
Alkyne -C=C -yne
 Prefixes used for functional groups

Class Prefix used Class Prefix used

-Br Bromo -CO- Oxo

(Ketone)
-Cl Chloro -NO2 Nitro

-F Fluoro -NO Nitroso

-I Iodo -CN Cyano

-R Alkyl -OH Hydroxy

(Alcohol)
-OR Alkoxy -NH2 Amino
(Amine)

•Prefix of functional is used when these functional group is not a

principal functional group.
•When these functional groups considered as substituent then
their prefixes are used.
 Pattern of MSBTE question paper

Sr.no Question Marks TIME

MANAGEMENT

1. Attempt any EIGHT/ FIVE of the following 16 / 20

8/12…..5/8 Time 180 min
06 que
2. Attempt any FOUR OR 3 of the following 12
4/6 OR 5…..
30 min./ EACH
3. Attempt any FOUR OR 3 of the following 12 MAIN que
4/6 OR 5…..
4. Attempt any FOUR OR 3 of the following 12 For 4 QUESTIONS OF
4/6 OR 5….. 3 marks
que 7 mimN EACH
5. Attempt any FOUR OR 3 of the following 12
4/6 OR 5….. for 3 QUESTIONS OF
6. Attempt any FOUR OR 3 of the following 16/12 4 marks 10 min
4/6 OR 5….. EACH

06 Total 06 questions 80/136/1 FOR 8 QUE.OF 2

32 marks 4 min
EACH
TYPES OF QUESTIONS-

Draw structure with numbering of the different heterocycle.

Write structure of the organic groups

Name the drug present in the following brands.

Give two brand names for each of the following drugs

In what dosage form the following drugs are administered?

Tolnaftate (ii) Insulin
Write properties and uses of uses of following:
Draw two structures of drug containing pyrimidine ring.
Give structure and uses
Name the drug used for (i) Glaucoma
Classify Antiseptics and Disinfectants. Draw structure of chlorocresol.
Give structure and use of propranolol and Pethidine.
Give properties, uses and official preparations of Clofibrate.
Define Analeptic. Give structure and chemical name of caffeine.
Give name, structure and properties of Sulphonamide used for the treatment of eye infection.
What is Leprosy? Give structure and uses of Dapsone.
Classify Antibiotics according to chemical structure with example
What do you know about adrenocorticoid hormones? Give uses and official preparations of
Hydrocortisone.
Give structure, chemical name and uses of Thyroxin.
Draw structure of given chemical name:
Differentiate between general and local anesthetics.
Notes like co trimaxazole,sex hormones