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Nomenclature of Organic Compounds 127
Diethyl carbamoyl (CH
3
CH
2
)
2
NCO– Isobutyl –CH
2
–CH(CH
3
)
2
Dimethylamino (CH
3
)
2
N– Isopropyl (CH
3
)
2
CH–
Ethoxy CH
3
CH
2
O– Isopentyl (CH
3
)
2
CH–[CH
2
]
2
–
Ethoxy carbonyl CH
3
CH
2
OCO– Mercapto HS–
Ethyl CH
3
CH
2
– Mercaptocarbonyl RC=OSH
Ethynyl –CH≡C– Methoxy –OCH
3
Fluoro F– Methyl –CH
3
Formyl OHC– Methylamino CH
3
NH–
Glycyl H
2
N–CH
2
–CO– Methylsulphonyl CH
3
SO
2
Guanidino H
2
N–C (=NH)–NH– Methylthio- CH
3
S–
Halocarbonyl –COX Nitro- –NO
2
Hydroxy –OH Nitrooxy- RONO
2
Hydroxy methyl –CH
2
OH Nitrosooxy- RONO
2-Hydroxy ethyl –CH
2
CH
2
OH Oxo- =O
Peroxy ROOR' Propionyloxy CH
3
CH
2
COO–
Phenethyl C
6
H
5
CH
2
CH
2
– Selanylcarbonyl –COSeH
Phenoxy C
6
H
5
O sulfanyl RSH
2-Phenoxyethyl C
6
H
5
OCH
2
CH
2
– Sulfino –SO
2
H
Phenoxymethyl C
6
H
5
OCH
2
– Sulfo –SO
3
H
Phenyl –C
6
H
5
– Sulfonyl) oxy RSO
3
R'
Propionyl CH
3
–CH
2
–CO– Thioxo =S
Phenyl acetamido C
6
H
5
CH
2
CONH– Tosyl CH
3
C
6
H
4
SO
2
P–
Phosphonic acid RP(=O)(OH)
2
Trifluoromethyl F
3
C–
Phosphonooxy ROP(=O)(OH)
2
Vinyl −CH=CH
2
Propoxy CH
3
CH
2
CH
2
O–
4.4 NAMING OF HETEROCYCLIC NUCLEI
The heterocyclic compounds are the cyclic compounds containing carbon and other
heteroatom; oxygen (O), nitrogen (N) and sulfur (S). The heterocyclic rings pyrrole, furan, and
thiophene each contain five-member rings, composed of four atoms of carbon and one atom of
nitrogen, oxygen, or sulphur, respectively. A molecule of pyridine contains a ring of six atoms—
five carbon atoms and one nitrogen atom.
128 Text Book of Pharmaceutical Chemistry
1. In the heterocyclic ring, hetero atoms are present in a ring and are indicated by prefixes;
in particular, oxa-, thia-, and aza- denote oxygen, sulphur, and nitrogen atoms,
respectively (Table 4.1).
2. In the heterocyclic rings the presence of different types of heteroatom is indicated by
combining the above prefixes, using the order of preference starts with the heteroatom
of as high a group in the periodic table and as low an atomic number in that group: thus
the order of naming will be:
O ˃ S ˃ Se ˃ N ˃ P ˃ Si ˃ B ˃ Hg (see table I)
According to this system single three- to- ten-membered rings are named by combining the
appropriate prefix or prefixes (listed in Table 4.1) with a stem from (Table 4.2).
Table 4.1: Prefix Name of Heteroatom and their Order of Priority
Heteroatom
Prefix Name
Order of Priority
Oxygen
Oxa
1
Sulphur
Thia
2
Selenium
Selena
3
Nitrogen
Aza
4
Phosphorus
Phospha
5
Silicon
Sila
6
Boron
Bora
7
Mercury
Mercura
8
The Suffix determines the state of saturation or unsaturation which depends upon:
(i) The presence or absence of N atom
(ii) The ring size.
Table 4.2: Common Name Endings for Heterocyclic Compounds
Ring Size
Suffix for fully
unsaturated compounds
Suffix for fully
saturated compounds
With N
Without N
With N
Without N
3
-irine
-irene
-iridine
-irane
4
-ete
-ete
-etidine
-etane
5
-ole
-ole
-olidine
-olane
6
-ine
-in
‒
-ane
7
-epine
-epin
‒
-epane
8
-ocine
‒
-ocin
-ocane
Nomenclature of Organic Compounds 129
3. The endings in (Table 4.2) also indicate the size of the ring and the state of
hydrogenation with or without the presence of a nitrogen atom. Accordingly, some
examples of compounds named on the basis of above two tables are cited below:
4. The ring is numbered from the atom of preference in such a way so as to give the
smallest possible number to the other hetero atoms in the ring. This is illustrated by the
following examples:
5. In a monocyclic compound, position of a single heteroatom controls the numbering but
not necessarily in a bicyclic compound.
6. Numbering in the heterocyclic rings becomes essential when substituents are placed on
the ring. The hetero atom is assigned position 1 and the substituents are then counted
around the ring in a manner so as to give them the lowest possible numbers.
7. While writing the name of the compound, the substituents are placed in an alphabetical
order.
8. Saturated or hydrogenated ring systems are named by varying the ending or by placing
prefixes such as ‘dihydro-’, ‘tetrahydro-’, etc. The ending of the name will depend on
the presence or absence of nitrogen (Table 4.2).
130 Text Book of Pharmaceutical Chemistry
9. When two or more similar hetero atoms contained in a ring are indicated by the prefixes
‘di-’, ‘tri’, etc. placed before the appropriate ‘a’ term.
10. A saturated heteroatom with an extra-hydrogen attached is given priority over an
unsaturated form of the same atom, as in 1H-1,3-diazole.
11. The numbers are grouped together in front of the hetero atom listings (thus, 1,3-oxazole,
not 1-oxa-3-azole). The hetero atom prefixes follow the numbers in the priorities given
previously.
12. There are a large number of important ring systems in heterocyclic chemistry which do
not possess any systematic names rather non-systematic or common names are used for
them. Some of such heterocyclic system with examples are given below:
Drugs
Heterocyclic systems
Drugs
Heterocyclic systems
Thiotepa
Aziridine
Furesemide,
Nitrofurazone,
Furazolidone,
Nitrofurantoin,
Ranitidine
Furan
Atorvastatin (Lipitor),
Tolmetin,
Amtolmetin,
Tallimustine
Pyrrole
Furazolidone,
Troxidone
Oxazolidine
Nomenclature of Organic Compounds 131
Drugs
Heterocyclic systems
Drugs
Heterocyclic systems
Pentolinium
Pyrrolidine
Sulphamethoxazole,
Oxacillin,
Cloxacillin,
Valdecoxib,
Mofezolac
Isoxazole
Celcoxib,
Phenylbutazone,
Apixaban,
Sulphinpyrazone,
Indisteron,
Phenazone, Betazole,
Lonazolac,
Pyrazofurin,
Rimonabant,
Ramifenazone
Pyrazole
Cycloserine
Isoxazolidine
Analgin
3-Pyrazoline
Cefoxitin,
Cephalothin,
Cephaloridine,
Temocillin
(antimicrobial
agents), Suprofen,
Raltitrexed,
Tiaprofenic Acid
Thiophene
Oxyphenbutazone
Pyrazolidine
Sulphathiazole
Thiazole
Alpidem,
Metronidazole,
Flumazenil,
Misonidazole,
Luliconazole,
Dacarbazine,
Tipifarnib, Nilotinib,
Ketoconazole
Imidazole
Acetazolamide,
Cephazolin
Methazolamide,
Megazol,
Sulfamethizole,
Cefazolin
1,3,4-thiadiazole
132 Text Book of Pharmaceutical Chemistry
Drugs
Heterocyclic systems
Drugs
Heterocyclic systems
Clonidine,
Waphazoline
2-Imidazoline
Ribavirin,
Fluconazole,
Voriconazole,
Itraconazole,
Trapidil,
Alprazolam,
Estazolam,
Vorozole, Letrozole,
Anastrazole
Tetrazole
Carbimozole
4-Imidazoline
Esomeprazole,
Loratadine,
Crizotinib
Pyridine
Nitrofurantoin
Imidazolidine
Haloperidol,
Thioridazine,
Raloxifene,
Misoridazine,
Donepezil,
Pipamperone,
Vinblastine
Piperidine
Idoxuridine
1,2,3,4-
tetrahydropyrimidine
Sulphamethoxy
pyridazine
Pyridazine
Primidone
Perhydropyrimidine
Acipimox,
Amiloride,
Benzamil,
Bortezomib,
Glipizide
Pyrazine
Nomenclature of Organic Compounds 133
Drugs
Heterocyclic systems
Drugs
Heterocyclic systems
Phenytoin
Hydantoin
Itraconazole,
Posaconazole
Piperazine
Phenobarbitone,
Amylbarbitone,
Mephobarbital
Barbituric acid
Minoxidil,
Itravirine, Rilpivirin,
5-fluorouracil,
Enazadrem
Pyrimidine
Drugs
Heterocyclic systems
Drugs
Heterocyclic systems
Indomethacin
Indole
Aminacrine,
Nitracrine,
Ethacridine,
Quinacrine
Acridine
Methisazone
Indoline
Albendazole,
Thiabendazole,
Mebendazole,
Nocodazole,
Maribamir,
Lerisetron
Benzimidazole
Chorthalidone
Isoindoline
Promazine,
Chlorpromazine,
Trifluperazine,
Promethazine,
Thioridazine
Phenothiazine
134 Text Book of Pharmaceutical Chemistry
Drugs
Heterocyclic systems
Drugs
Heterocyclic systems
Quinine,
Chloroquine,
Mefloquine,
Amodiaquine
Quinoline
Hydralazine,
Budralazine,
Azelastine,
Zopolrestat
Phthalazine
Papaverine
Isoquinoline
Tubocurarine
1,2,3,4-
Tetrahydroisoquinoline
Proquazone,
Febrifugine,
Gefitinib,
Erlotinib,
Doxazocin
Quinazoline
Caffeine,
Theophylline
4.5 EXERCISE
A. Long Answer Type Questions
1. What are heterocyclic compounds? Write the general rules with examples for naming of
heterocyclic compounds.
2. What are organic compounds? How organic compounds can be classified?
B. Short Answer Type Questions
1. What is non-proprietary name?
2. What are brand names?
3. What is the full form of IUPAC?
4. Write the name of the following heterocyclic structures:
(a)
Nomenclature of Organic Compounds 135
(b)
(c)
(d)
(e)
C. Fill in the Blanks
1. Write the structure of Pyridine ________________
2. Write the structure of Pyrimidine ________________
3. Write the structure of Furan ________________
4. Write the structure of Imidazole ________________
5. Write the structure of Pyrrole ________________
6. Write the structure of Quinoline ________________
7. Write the structure of Thiazole ________________
8. Write the structure of Hydantoin ________________
Answers:
1.
2.
136 Text Book of Pharmaceutical Chemistry
3.
4.
5.
6.
7.
8.