9-OXOBENZOMORPHANS .2. VERSATILE PROCESS FOR THE SYNTHESIS OF 9-OXO-6,7-BENZOMORPHANS
9-OXOBENZOMORPHANS .2. VERSATILE PROCESS FOR THE SYNTHESIS OF 9-OXO-6,7-BENZOMORPHANS
复制标题
DOI：
10.1139/v79-294
复制
发表时间：
1979-01-01
影响因子：
1.1
通讯作者：
BELLEAU, B
中科院分区：
文献类型：
--
作者：
KAVADIAS, G;VELKOF, S;BELLEAU, B
本文介绍了新镇痛药5-烯丙基-2“-甲氧基-2-甲基-9-氧代-，2”-甲氧基-2，5-二甲基-9-氧代-，5-烯丙基-2-环丙基甲基-2“-甲氧基-9-氧代-，5-（3-亚乙二氧基）丁基-2”-甲氧基-3-甲基-9-氧代-6，7-苯并吗啉（5a-d）的合成方法。它涉及将5，9 b-二氢苯并[e]吲哚啉溴化为硼亚胺，然后用碳酸氢铵水解，将其转化为4-溴-5，9 b-二氢苯并[e]吲哚啉（快速步骤）。这些经历水合（在缓慢的步骤中），随后重排为5a-d。当用Na、K和氢氧化铵代替碳酸氢铵时，反应的过程是不同的。
The synthesis of the new analgesics 5-allyl-2''-methoxy-2-methyl-9-oxo-, 2''-methoxy-2,5-dimethyl-9-oxo-, 5-allyl-2-cyclopropylmethyl-2''-methoxy-9-oxo- and 5-(3-ethylenedioxy)butyl-2''-methoxy-3-methyl-9-oxo-6,7-benzomorphans (5a-d) by an improved process is described. It involves bromination of the 5,9b-dihydrobenz[e]indolines to the bormoiminium bormides, followed by hydrolysis with ammonium bicarbonate which converted them to 4-bromo-5,9b-dihydrobenz[e]indolines (in a fast step). These underwent hydration (in a slow step) followed by rearrangement to 5a-d. The course of the reactions was different when Na, K, and ammonium hydorxides were substituted for ammonium bicarbonate.