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Chapter 6
Synthesis of benzodiazepines
6.6 Results and discussion
Scheme: Synthesis of some new benzodiazepine derivatives
Scheme-01
Scheme-02
Where R= CH 3 , CH(CH 3 ) 2 , R 1 = CH 3 , F, Cl, NO 2 , X=Br
Synthesis of 1-and 3-substituted 1,4-benzodiazepinederivatives is shown in
sheme 1 and 2. The starting material, 2-amino-4’-flouro-benzophenone ADZ-01 was
reacted with chloroacetyl chloride in toluene at room temperature to afforded 2-
chloro-N-(2-(4’-fluorobenzoyl)phenyl)acetamide. The latter was converted in to 1,4-
benzodiazepines ADZ-03 by following the literature methods using ammonium
acetate and hexamine in EtOH. 54-55 The N-alkylation of 1,4-benzodiazepines with
various alkyl halide in DMF at below 15 o C in the presence of potassium hydroxide
proceeded smoothly to furnish a series of 1-substituted-5-(4-fluorophenyl)-1Hbenzo[e][1,4]diazepin-2(3H)-one
ADZ-04a-j in good yields. Reaction time and (%)
of yield is summarized in Table-1.
On the other hand, the condensation of of 1,4-benzodiazepines ADZ-03 with
aromatic aldehydes in the presence of potassium hydroxide in reluxing provided a
series of new 3-substituted-5-(4-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one
ADZ-05a-j in excellent yields (Table-2).
Department of Chemistry, Saurashtra University, Rajkot-360005 212