Total synthesis of asperlicin D

A combined experimental and theoretical study of the synthesis of quinazolino[3,2-a][1,5]benzodiazepin-13-ones

“…These differences can not be explained entirely by the steric hindrance caused by 3-methyl group. The steric influence of 3-methyl group was not observed in our previous study of the synthesis of imidazo[1,2-a] and thiazolo[3,2-a] [1,5]benzodiazepine derivatives. 8,9 Moreover, it is well known that the steric hindrance effects of bulky methyl group most often affects reactivity behaviors in the less flexible aromatic system or in the molecular systems bearing conjugated delocalized π bonding.…”

“…1 These alkaloids display various biological activities. In a quest to find additional potential quinazoline-based derivatives, various substituted quinazolinones 2,3 and compounds encompassing a quinazolino [1,4]benzodiazepine moiety in their skeleton [4][5][6][7] have been developed. As a part of our ongoing research activity, [8][9][10] we were interested in the synthesis of some quinazolino [1,5]benzdiazepine derivatives as possible analogues of natural products.…”

“…In a quest to find additional potential quinazoline-based derivatives, various substituted quinazolinones 2,3 and compounds encompassing a quinazolino [1,4]benzodiazepine moiety in their skeleton [4][5][6][7] have been developed. As a part of our ongoing research activity, [8][9][10] we were interested in the synthesis of some quinazolino [1,5]benzdiazepine derivatives as possible analogues of natural products. The main synthetic routes to compounds with quinazolino [1,4]benzodiazepine moiety utilize the implementations of 2-azidobenzoylamides in aza-Wittig methodology 4,5,11 and transition metal-…”

“…As a part of our ongoing research activity, [8][9][10] we were interested in the synthesis of some quinazolino [1,5]benzdiazepine derivatives as possible analogues of natural products. The main synthetic routes to compounds with quinazolino [1,4]benzodiazepine moiety utilize the implementations of 2-azidobenzoylamides in aza-Wittig methodology 4,5,11 and transition metal-…”

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AbstractA simple and efficient general approach to various tetracyclic 6,7-dihydroquinazolino[3,2-a] [1,5]benzodiazepin-13(5H)-ones has been demonstrated by reductive N-heterocyclization of 5-alkyl-or benzoyl-1-(2-nitrobenzoyl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-ones. These 2-nitrobenzoylamides were obtained by acylation of the starting 5-alkyl-or benzoyl-1,5-benzodiazepin-2-ones with 2-nitrobenzoyl chloride.

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