One-pot synthesis of 1,5-benzazepines(benzodiazepine, benzoxazepine,benzothiazepine)

【作者】 Laiyun Zhou； 王兰芝；

【Author】 Laiyun Zhou;Lanzhi Wang;The College of Chemistry and Material Science Hebei Normal University;

【机构】 The College of Chemistry and Material Science Hebei Normal University； 河北师范大学；

【摘要】 1,5-benzazepines is a kind of extremely significant compounds, which have high biologicaland pharmacological activity in the last decades.^[1] Such as antidepressant, anticonvulsant, sleep,anti-cramping and sedation.1,5-benzazepines compounds as anti-anxiety synthetic drugs have been used clinically.Recent studies have shown that these compounds also have excellent anti-inflammatory activity.^[2] Therefore, in recent years, more and more researchers pay attention to the synthesis of 1,5-benzazepines.^[3] So in this article, one-pot synthesis of 1,5-benzazepines compounds including 1,5-benzodiazepine, 1,5-benzoxazepine, 1,5-benzothiazepine are developed under refluxing toluene from 2-aminobenzenethiol, 2-aminobenzenephenol or 1,2-diaminobenzene and ethyl acetoacetate as raw materials（Scheme 1）.The reaction mixture was refiuxed for 4 hours and the solvent was distilled off, and then the residue was left overnight at room temperature and products were recrystallised with dry toluene.The target compounds are determined by ¹H NMR, ¹³C NMR, MS, and IR.Simple operation, short reaction time, high yields（85%-93%） are the advantages of this synthesis method.This work not only enriches the type of 1,5-benzazepines, but also provides a reference for the future synthesis.更多还原

【Abstract】 1,5-benzazepines is a kind of extremely significant compounds, which have high biologicaland pharmacological activity in the last decades.^[1] Such as antidepressant, anticonvulsant, sleep,anti-cramping and sedation.1,5-benzazepines compounds as anti-anxiety synthetic drugs have been used clinically.Recent studies have shown that these compounds also have excellent anti-inflammatory activity.^[2] Therefore, in recent years, more and more researchers pay attention to the synthesis of 1,5-benzazepines.^[3] So in this article, one-pot synthesis of 1,5-benzazepines compounds including 1,5-benzodiazepine, 1,5-benzoxazepine, 1,5-benzothiazepine are developed under refluxing toluene from 2-aminobenzenethiol, 2-aminobenzenephenol or 1,2-diaminobenzene and ethyl acetoacetate as raw materials（Scheme 1）.The reaction mixture was refiuxed for 4 hours and the solvent was distilled off, and then the residue was left overnight at room temperature and products were recrystallised with dry toluene.The target compounds are determined by ¹H NMR, ¹³C NMR, MS, and IR.Simple operation, short reaction time, high yields（85%-93%） are the advantages of this synthesis method.This work not only enriches the type of 1,5-benzazepines, but also provides a reference for the future synthesis.更多还原