Nomenclature of common heterocycles-2

All heterocycles in this course are known by their common names.

IUPAC names are formed from:

Heteroatom(s) as prefix + stem + suffix

Nitrogen (N) = Aza
Oxygen (O) = Oxa
Sulphur (S) = Thia
Membered Nitrogen Nitrogen None None
ring Containing Containing Nitrogen Nitrogen
Unsaturated Saturated Unsaturated Saturated
6-membered Stem = in Stem = in Stem = in Stem +
Azine Prefix Suffix =
Pyridine Dihydro- an
(common) Tetrahydro- Dioxan
Perhydro-

6-membered rings are also named by common names but also we can
apply IUPAC rules for naming.

N O

Azine (pyridine) Dioxan

Membered Nitrogen Nitrogen None None
ring Containing Containing Nitrogen Nitrogen
Unsaturated Saturated Unsaturated Saturated
7-membered Stem = epin Stem = epin Stem = epin Stem +
1,4- Prefix Suffix =
diazepine Dihydro- Epan
Tetrahydro-
Perhydro-

7-membered rings are named by IUPAC rules for naming.

N

1,4-benzodiazepine
6-Membered rings
The heterocycles mentioned on the following
structure are respectively, named as:
N
A B

S
N
N
H3C N
C
O

1- isothiazole, pyridine, piperidine

2- thiazole, pyridine, piperidine
3- thiazole, pyridine, pyrimidine
4- thiazine, pyrrole, pyrimidine
The following structure is known as:

NH

a)- Pyridine
b)- 1,2-dihydropyridine
c)- 1,4-dihydropyridine
d)- Pyrazine
The following structure is known as:

NH

a)- Pyridine
b)- 1,2-dihydropyridine
c)- 1,4-dihydropyridine
d)- Pyrazine
The following structure is known as ?

N
O

1- oxazole
2- isoxazole
3- 4H-1,6-oxazine
4- 4H-1,2-oxazine
The following structure is known as ?

NH
O

1- oxazole
2- isoxazole
3- 6H-1,6-oxazine
4- 4H-1,2-oxazine
5- None of the above
The following structure is known as:

a)- Pyridine
b)- 1,2-dihydropyrine
c)- 1,4-dihydropyrine
d)- Pyrazine
The following structure is known as:

a)- isoxazolidine
b)- isoxazoline
c)- isoxazole
d)- oxazolidine
The following structure is known as:

N
a)- Pyridine
b)- Aziridine
c)- Azet
d)- Pyrrole
Have a look to the following reactions:

H, H2O
Reaction A
O O O

Raney Ni
Reaction B
S

1- Agree for both reactions

2- Agree for reaction A but not reaction B
3- Agree for reaction B but not reaction A
4- Disagree for both reactions
Provide the structure of the major organic product in the
reaction below.

Ph COCl
?
N
Ph

O
Ph
Cl Ph N Cl
N N N
O O H
A B C D
1- product A
2- product B
3- product C
4- product D
Formylation by HCN and HCl
1- HCl, HCN, AlCl3
2- H2O CHO
O O

Cl H
HCl, AlCl3 C N
H C N H H

Cl H
C N H H H H2O
H H C N C N
O O O
H H H H

O H
CH
O NH3
Formylation by carbon monoxide

CO, HCl, AlCl3

CHO
O O

Cl
O
AlCl3
H
Cl
O
AlCl3
H
O
• Mannich Reaction
NH2 +
H N

O O
Cl
Cl
H Me
HNMe2, HCHO, HOAc
N
H Me

H Me NMe2 NMe3 CN
N
N H Me N N N
CH3I CN

Cl Cl Cl Cl

CN CONH2 COOH
N N N
H2O H2O

Cl Cl Cl