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Chapter 6 Synthesis of benzodiazepines New 2,4-disubstituted 1,5-benzodiazepine derivatives containing different functional groups have been synthesized and screened for their antibacterial activity. The 2,4-disubstituted 1,5-benzodiazepine derivatives were synthesized by reacting substituted chalcones synthesized using aldol condensation with o-phenylenediamine (Figure-19). QSAR studies of synthesized derivatives were performed. 61 Figure-19 A facile and efficient synthesis of 1,5-benzodiazepines with an aryl sulfonamido substituent at C(3) is described. 1,5-Benzodiazepine, derived from the condensation of benzene-1,2-diamine and diketene, reacts with an arylsulfonylisocyanate via an enamine intermediate to produce 1,5-benzodiazepines good yields (Figure-20). 62 Figure-20 Goswami and Das reports the organo catalyzed one-pot synthesis of substituted 1,5-benzodiazepinesby condensation of o-phenylenediamine, and 1,3- dicarbonyl compounds at room temperature or under reflux in the presence of catalytic amount of L-proline as shown in (Figure-20). 63 Figure-20 Department of Chemistry, Saurashtra University, Rajkot-360005 210
Chapter 6 Synthesis of benzodiazepines 6.5. Current research work The chemistry of benzodiazepines and its derivatives has been studied for over a century due to their diverse biological activities. It has numerous pharmacological and medicinal applications viz, PAF antagonists, cardiovascular agents, CNS-active agent, hypnotic, anxiolytic, sedative and anticonvulsant. Therefore, we set to prepare some new 1H-benzo[e][1,4]diazepin-2(3H)-one derivatives for their biological studies. The requisite starting material1,4-benzodiazepines (ADZ-03) was prepared by following the reported procedure. The 2-amino-4’-flouro-benzophenone (ADZ-01) was reacted with chloroacetylchloride to afford 2-chloro-N-(2-(4’-fluorobenzoyl) phenyl)acetamide (ADZ-02). It was subsequently converted to 1,4-benzodiazepines by the modification of the known hexamethylenetetramine-(HMTM)-based cyclization reaction developed by Blazevic and Kajfez. 54-55 ADZ-03 thus obtained was reacted with a variety of alkyl halide using KOH in DMF to give 1-substituted-5- (4-fluorophenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (ADZ-04a-j). To achieve 5- substituted 1,4-benzodiazepines (ADZ-05a-j), 5-(4-fluorophenyl)-1H-benzo[e][1,4] diazepin-2(3H)-one (ADZ-03) was treated with various aromatic aldehydes in the presence of potassium hydroxide in toluene. The newly synthesized compounds were characterized by IR, Mass, 1 H NMR, 13 C NMR spectroscopy and elemental analysis. Department of Chemistry, Saurashtra University, Rajkot-360005 211
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Saurashtra University Re - Accredit
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Statement under O.Ph.D.7 of Saurash
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I am thankful to FIST/DST and SAP/U
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Chapter 4 Synthesis and Characteriz
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Chapter - 1 Palladium Catalyzed Syn
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Chapter 1 Synthesis of functionaliz
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