Synthesis of 3-Substituted 1,4-Benzodiazepin-2-ones

Abstract

A preparação de benzodiazepínicos 1,4 substituídos na posição 3 é explorada a partir da alquilação de enolatos benzodiazepínicos. Empregando-se tal abordagem, vários gramas de benzodiazepínicos 1 foram preparados para estudos em animais, visando avaliar uma nova abordagem no tratamento da doença auto-imune lúpus eritematoso (LE). The preparation of 3-substituted 1,4-benzodiazepines by benzodiazepine enolate alkylation has been explored. Employing this approach, multigram quantities of benzodiazepine 1 have been prepared for animal studies to evaluate a new approach for the treatment of the autoimmune disease systemic lupus erythematosus (SLE).

A Serendipitous Synthesis of 11a-Hydroxy-11,11a-dihydrobenzo[e]indeno[2,1-b][1,4]diazepine-10,12-dione Derivatives by Condensation of 2-Aminobenzamides with Ninhydrin in Water

“…The seven membered 1,4-diazepine ring occurs as the main structural core in a variety of biologically active synthetic and natural products. − The 1,4-benzo­diazepine scaffold has been synthesized , through the postcondensation transformations of four-component Ugi reaction products. A multigram synthesis of 1,4-benzo­diazepines has been reported wherein 2-amino­benzo­phenone is treated with bromoacetyl bromide in diethyl ether followed by amination and cyclization under acidic conditions. The most extensively used methods for the synthesis of benzodiazepines involve the condensation of o -phenylene­diamines with α,β-unsaturated carbonyl compounds; with ketones in the presence of NaBH 4 , polyphosphoric acid, or SiO 2 ; Al 2 O 3 /P 2 O 5 or AcOH under microwave conditions; amberlyst-15 in the ionic liquid 1-butyl-3-methyl­imidazolium bromide; CeCl 3 ·7H 2 O/NaI supported on silica gel;and InBr, Sc­(OTf) 3 , and sulfated zirconia .…”