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Chapter 6
Synthesis of benzodiazepines
A variety of 3-arylidine benzodiazepines bearing electron donating and electron
withdrawing groups such as 3,4-diOCH 3 ; 4-OCH 3 ; H; 2,5-diOCH 3 ; 2-OH; 4-F; 4-Br;
4-Cl; 4-NO 2 and 3-NO 2 were prepared.
Table-1: Synthesis of 1-substituted benzodiazepine derivatives
Entry R Yield (%) Time hrs
ADZ-04a -CH 3 87 2.0
ADZ-04b -CH 2 CH 3 83 2.5
ADZ-04c -(CH 2 ) 2 CH 3 88 3.0
ADZ-04d -CH(CH 3 ) 2 84 2.5
ADZ-04e -(CH 2 ) 3 CH 3 80 3.0
ADZ-04f -CH 2 CH(CH3) 2 89 3.5
ADZ-04g (CH 2 ) 4 CH 3 90 2.5
ADZ-04h -(CH 2 ) 2 CH(CH 3 ) 2 88 4.0
ADZ-04i C 6 H 11 79 4.5
ADZ-04j -CH 2 C 6 H 4 4-NO 2 90 4.0
The structures of ADZ-03 were conformed on the basis of their elemental
analysis and spectral data (MS, IR, and 1 H NMR).The analytical data for ADZ-03
revealed a molecular formula C 15 H 11 FN 2 O 2 (m/z 254).The 1 HNMR spectrum revealed
a singlet at 4.31ppm assigned to –CH 2 group, a four multiplet signals at δ = 7.04–
7.57 ppm assigned to the aromatic protons, and one broad singlet at δ = 8.83 ppm
assigned to -CONH groups.
Table-2: Synthesis of 3-arylidine benzodiazepine derivatives
Entry R 1 Yield (%) Time hrs
ADZ-05a H 90 2.0
ADZ-05b 3-NO 2 85 2.5
ADZ-05c 3,4-diOCH 3 83 3.0
ADZ-05d 4-OCH 3 87 2.5
ADZ-05e 4-Cl 94 3.0
ADZ-05f 4-F 90 3.5
ADZ-05g 4-NO 2 92 2.5
ADZ-05h 4-Br 89 4.0
ADZ-05i 2-OH 80 4.5
ADZ-05j 2,5-diOCH 3 81 4.0
Department of Chemistry, Saurashtra University, Rajkot-360005 213