HETEROCYCLIC COMPOUNDS:

NOMENCLATURE
TUTORIAL 1

Pharmaceutical Chemistry III PHCM773

 Intended Learning Outcomes

• Know the difference between the Carbocyclic and Heterocylic compounds.

• Understand the rules of nomenclature of both Monocyles and fused

Heterocycles.

• Introduce briefly the different common names of both Monocyles and fused
Heterocycles.

• Differentiate between the generic name, trade name and a chemical name of a
specific drug.

• Apply the IUPAC naming rules on various drug.

Pharmaceutical Chemistry III PHCM773

 HETEROCYCLIC COMPOUNDS
 They are organic compounds that contain one or more rings containing
other atoms other than carbon; e.g. nitrogen, sulphur, oxygen , ……. etc.

 They can be classified into:

A. Monocycles
B. Fused heterocycles
1) Fused carbocycle and heterocycle
2) 2 Fused heterocycles

Pharmaceutical Chemistry III PHCM773

 A) NOMENCLATURE OF
MONOCYCLES
IUPAC NOMENCLATURE SYSTEM
1. Name (Prefix + stem + suffix)
 Prefix  includes the type, number (di, tri...etc) and positions of hetero atoms. Most common hetero
atoms in order of priority are:
O (oxa) >> S (thia) >> N (aza)
 Stem  includes the ring size
Most common: 5-membered ring --ol
N
Azine
6-membered ring --in
7-membered ring --ep
NH
 Suffix  shows saturation or unsaturation
Fully Unsaturated Fully Saturated
O
5-membered ole olidine 1,3-Oxazolidine
6-membered ine perhydro ……ine
7-membered epine perhydro …..epine
Pharmaceutical Chemistry III PHCM773
 A) NOMENCLATURE OF
MONOCYCLES
IUPAC NOMENCLATURE SYSTEM
2. Numbering
 If one heteroatom in the ring  heteroatom takes no. 1 and give the other substituents the least
possible number

 If more than one heteroatom in the ring  the most prior heteroatom takes no. 1, give the
other heteroatoms the least possible no. regardless of their priority! (O > S > N)

Cl Cl N Cl S

N NH2 S N
O O

2-Amino-3-chloro 5-Chloro-1,2,4 5-Chloro-1,4,2

azine -oxathiazine -oxathiazine

Pharmaceutical Chemistry III PHCM773

 A) NOMENCLATURE OF
MONOCYCLES
IUPAC NOMENCLATURE SYSTEM
3. Partially Saturated rings
Number of double bonds

Less than maximum Maximum

prefix dihydro, tetrahydro , saturated position is
….etc are added to the same indicated by symbols 1H ,
name of unsaturated state. 2H, 3H ….etc.

N
NH

N
H
1,2-Dihydroazine 1H -1,3-Diazole
Pharmaceutical Chemistry III PHCM773
 A) NOMENCLATURE OF
MONOCYCLES
COMMON NAMES
One Nitrogen Two Nitrogens
NH NH HN

Unsaturated N N

pyrrole pyrazole imidazole

NH NH HN

Saturated NH NH

pyrrolidine pyrazolidine imidazolidine

S S S O HN

N
N
N
thiazole isothiazole thiophene furan imidazoline

Pharmaceutical Chemistry III PHCM773

 A) NOMENCLATURE OF
MONOCYCLES
COMMON NAMES
One Nitrogen Two Nitrogens
N
N N N N

Unsaturated
N
N
pyridine pyridazine pyrimidine pyrazine

HN

Saturated
NH NH

piperidine piperazine

O O
O
HN O
O
morpholine dioxane pyran 4H- Pyran
Pharmaceutical Chemistry III PHCM773 2H-Pyran
 B) NOMENCLATURE OF FUSED CARBOCYCLE
AND HETEROCYCLE
IUPAC NOMENCLATURE SYSTEM
 The parent name: the name of the heterocycle
 The fused name: the name of the carbocycle (benzene)

 The total numbering of the fused system starts at an atom next to fusion side  giving
heteroatom the lowest possible number and giving the fused carbons the same previous number
adding to it letters.
 Side of fusion of parent and fused rings: indicated by alphabetical numbering (a,b,c, ….etc.)
written in brackets between the prefix and parent ?!!

N
N
benzo (b) pyridine benzo (c) pyridine
Pharmaceutical Chemistry III PHCM773
 B) NOMENCLATURE OF FUSED CARBOCYCLE
AND HETEROCYCLE
COMMON NAMES
N
N
N
HN
N
N N
H H
indole isoindole indolizine purine
N
N
N N

N N

quinoline isoquinoline phthalazine quinazoline

O O N
N

O N N
tetralin 2H chromene Benzodioxane Pteridine
Pharmaceutical Chemistry III PHCM773
 B) NOMENCLATURE OF FUSED CARBOCYCLE
AND HETEROCYCLE
COMMON NAMES
H
N O

carbazole dibenzofuran

N O
acridine xanthene

Pharmaceutical Chemistry III PHCM773

 IUPAC NAMING OF DRUGS
(CHEMICAL NAME)

Pharmaceutical Chemistry III PHCM773

 HOW TO CHOOSE PARENT NAME ?

1. Functional group:

Carboxylic acids >> Esters >> Amides >> Aldehydes

>> Ketones >> Alcohols >> Amines >> Ethers.

2. Heterocycle
3. Carbocycle
4. Longest carbon chain

Pharmaceutical Chemistry III PHCM773

 NAMING OF FUNCTIONAL GROUPS:
Functional Formula Prefix Suffix
groups “Substituent” “Parent”
Carboxylic acid -COOH Carboxy Oic acid

Amide -NHCO- Carbamoyl Amide

Nitrile -C N Cyano Nitrile

Aldehyde -CHO- Formyl Al

Ketone -CO- Oxo One

Alcohol -COH- Hydroxy Ol

Thiol -SH- Sulfanyl Thiol

Amine -NR2- Amino Amine

Ether -O- Oxy Ether

Pharmaceutical Chemistry III PHCM773

 APPLICATIONS:
WRITE THE CHEMICAL NAME OF THE
FOLLOWING STRUCTURES

Lidocaine
2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide

Timolol
1-(tert-butylamino)-3-[(4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl)oxy]propan-2-ol
Pharmaceutical Chemistry III PHCM773
 APPLICATIONS:
WRITE THE CHEMICAL NAME OF THE
FOLLOWING STRUCTURES

Indomethacin
2-{1-[(4-Chlorophenyl)carbonyl]-5-methoxy-2-methyl indol-3-yl} acetic acid

Pharmaceutical Chemistry III PHCM773

 APPLICATIONS:
DRAW THE STRUCTURES
OF THE FOLLOWING CHEMICAL NAMES

O
O
O N O OH
H
OH N
H
Cl

Propranolol Bezafibrate
1-(Isopropylamino)-3-(1-naphthyloxy) 2-[4-[2-[(4-Chlorobenzoyl)amino]
-2-propanol ethyl]phenoxy]-2-methylpropanoic acid

Pharmaceutical Chemistry III PHCM773

 Reminder!!

Propranolol

Generic name: Propranolol

Trades names: Angilol, Cardinol, Ciplar, Duranol, Inderal…etc.

Chemical name:
1-(Isopropylamino)-3-(1-naphthyloxy)-2-propanol
2-Propanol, 1-(isopropylamino)-3-(1-naphthyloxy)-

Pharmaceutical Chemistry III PHCM773

 TEST YOURSELF!

N CH3

NH
Cl S
O O

Diazoxide Naphazoline
7-Chloro-3-methyl-2H-1,2,4-benzothiadiazine 2-(Naphthalene-1-ylmethyl)-4,5-dihydro
-1,1-dioxide -1H-imidazole

Pharmaceutical Chemistry III PHCM773