Mamedov Vakhid A, Zhukova Nataliya A, Syakaev Victor V, Gubaidullin Aidar T, Samigullina Aida I, Beschastnova Tat'yana N, Perevalova Darya S, Babaeva Olga B, Rizvanov Il Dar Kh, Sinyashin Oleg G
A. E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center, Russian Academy of Sciences, 420088 Kazan, Russian Federation.
J Org Chem. 2024 Oct 4;89(19):14577-14585. doi: 10.1021/acs.joc.4c01721. Epub 2024 Sep 19.
Presented herein is a novel synthesis of new 2-(quinolin-4-yl)-1,4-dihydroquinazoline systems , in which the acid-catalyzed rearrangement of spiro[benzo[][1,4]diazepine-3,4'-quinolin]-2(1)-ones generated from 3-(2-aminophenyl)-5-benzo[][1,4]diazepin-2(1)-ones with acetone and alkylmethyl ketones has been realized as an important step. An attempt to synthesize isomeric 2-(2-aminophenyl)-5-benzo[][1,4]diazepin-3(4)-one by hydrolysis of the corresponding -{2-[5-benzo[][1,4]diazepin-3(4)-on-2-yl]phenyl}acetamide led to a new heterocyclic system, 6-methyl-8,13-dihydro-13a-quinazolino[4,3-]quinazolin-5-ium 13a-carboxylate , as a result of an unexpected rearrangement. In addition, it is noteworthy that during the hydrolysis of -{2-[5-benzo[][1,4]diazepin-2(1)-on-3-yl]phenyl}acetamides , the not previously described 14-dihydro-5-14,5a-(epimino[1,2]benzo)benzo[5,6][1,4]diazepin[2,1]quinazolin-6(7)-ones were unexpectedly obtained.
本文介绍了一种新型的2-(喹啉-4-基)-1,4-二氢喹唑啉体系的合成方法，其中由3-(2-氨基苯基)-5-苯并[][1,4]二氮杂卓-2(1)-酮与丙酮和烷基甲基酮生成的螺[苯并[][1,4]二氮杂卓-3,4'-喹啉]-2(1)-酮的酸催化重排反应是一个重要步骤。尝试通过相应的-{2-[5-苯并[][1,4]二氮杂卓-3(4)-酮-2-基]苯基}乙酰胺水解合成异构体2-(2-氨基苯基)-5-苯并[][1,4]二氮杂卓-3(4)-酮，结果由于意外的重排反应得到了一个新的杂环体系，即6-甲基-8,13-二氢-13a-喹唑啉并[4,3-]喹唑啉-5-鎓13a-羧酸盐。此外，值得注意的是，在-{2-[5-苯并[][1,4]二氮杂卓-2(1)-酮-3-基]苯基}乙酰胺的水解过程中，意外地得到了此前未描述过的14-二氢-5-14,5a-(表亚氨基[1,2]苯并)苯并[5,6][1,4]二氮杂卓[2,1]喹唑啉-6(7)-酮。
