11-Aryl-3,3-dimethyl-7- and 7,8-Substituted 1,2,3,4,10,11-Hexahydro-5H-dibenzo[b,e]-1,4-diazepin-1-ones

Microwave-assisted multi-component reaction in water leading to highly regioselective formation of benzo[f]azulen-1-ones

“…Heterocycles containing benzodiazepine rings belong to important building blocks because of their remarkable depressant activity in central nervous system 1 and their being one of the most widely prescribed class of psychotropics. 1h-i In addition, some of these compounds also possess bioactivities on analgesic, sedative ans antidepressive as well as hypnotic activities.…”

“…13a The reaction is easily performed by simply mixing readily available starting materials, aromatic aldehydes, cyclopentanone and cyanoacetamide with K 2 CO 3 in ethylene glycol under microwave (MW) irradiation. Interestingly, when aliphatic aldehydes were employed to replace their aromatic counterparts for the above MDR reaction, the reaction was found to undergo along another pathway leading to the formation of multi-functionalized tricyclo[6.2.2.0 1,6 ]dodecanes. 13b Recently, we have also found that the MDR of Meldrum’s acid, aromatic aldehydes and electron-rich heteroaryl-amines in aqueous phase under microwave irradiation (MW) led to the multifunctionalized spiro{[1,3]dioxanes-pyridine}-4,6-dione with high chemo- regio- and stereoselectivity and good yields.…”

Synthesis of novel tricyclic 4‐chloro‐7,8,10,11‐tetrahydro‐5H‐benzo[e]pyrimido[4,5‐b][1,4]diazepin‐9(6H)‐ones

“…Consequently, syntheses of benzodiazepine derivatives or diazepine-containing heterocycles are of interest to organic and medicinal chemists. Thus, dibenzo[b,e] [1,4]diazepines and other tricyclic systems with a 1,4-diazepine moiety are well documented in the literature [2][3][4][5][6][7][8][9].…”

“…These methodologies entail Bischler-Napieralski cyclization reactions and iminium cyclization reactions as the key transformation steps. To expand the scope of the iminium-cyclization reaction, we envisioned that enaminones 1 could be reacted with various aldehydes to prepare 7,8,10,11tetrahydro-5H-benzo[e]pyrimido [4,5-b] [1,4]diazepin-9(6H)ones [16], as depicted in Scheme 1. Although syntheses of dibenzo [b,e] [1,4]diazepines are frequently reported, there is few report of aminopyrimidines as substrates for such cyclization reactions [16].…”

“…Given the large structural differences between a pyrimidine and benzene, optimization of the cyclization reaction was investigated. Herein, we reported the development of this method to prepare 7,8,10,11-tetrahydro-5H-benzo[e]pyrimido [4,5-b] [1,4]diazepin-9(6H)-ones.…”