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Chapter-5
Synthesis of highly substituted pyrroles
5.6 Results and discussion
Scheme:Synthesis of highly substituted Atorvastatin analogs
Scheme-01
1
O
OH
MDC
SOCl 2
O
Cl
ZnO
F
O
F
Br 2 /CH 3 COOH
2 3 4
Br
O
F
Scheme-02
Scheme-03
N
H
O
R 1
5
R
O
O
H 2 N
O
O
O
O
R 1
Pivalic acid
Cyclohexane/THF
MW
N
H
O
R
N
O
O
O
O
F
ADD-01- 30
F
AS-01-30
Where R=CH 3 , (CH 3 ) 2 CH, (CH 2 ) 2 CH, R 1 =CH 3 , OCH 3 , Cl, NO 2
Scheme 1 and 2 shows the synthetic route for the requisite starting materials.
First, acid chloride of phenyl acetic acid (2) was prepared from phenylacetic acid (1)
using thionyl chloride in MDC as described in literature. 107 The fridle-craft reaction of
Compound 2 with fluorobenzene in the presence of ZnO 108 afforded 1-(4-
fluorophenyl)-2-phenylethanone (3) with good yield. The bromination of compound 3
using Br 2 /AcOH provided 2-bromo-1-(4-fluorophenyl)-2-phenylethanone (4). 109
Various acetoactanilide derivatives (AAA-01-30) were prepared as described
in chapter-4. The condensation reaction of these acetoactanilide derivative (AAA-01-
30) with 2-bromo-1-(4-fluorophenyl)-2-phenylethanone (4) using potassium
carbonate as a base in isopropyl alcohol afford the requisite 1,4-dicarbonyl
compounds (ADD-01-30).
Department of Chemistry, Saurashtra University, Rajkot-360005 169