ERGOLINE SYNTHONS - SYNTHESIS OF 3,4-DIHYDRO-6-METHOXYBENZ[CD]INDOL-5(1H)-ONE (6-METHOXY-UHLE KETONE) AND 3,4-DIHYDROBENZ[CD]INDOL-5(1H)-ONE (UHLE KETONE) VIA A NOVEL DECARBOXYLATION OF INDOLE-2-CARBOXYLATES
ERGOLINE SYNTHONS - SYNTHESIS OF 3,4-DIHYDRO-6-METHOXYBENZ[CD]INDOL-5(1H)-ONE (6-METHOXY-UHLE KETONE) AND 3,4-DIHYDROBENZ[CD]INDOL-5(1H)-ONE (UHLE KETONE) VIA A NOVEL DECARBOXYLATION OF INDOLE-2-CARBOXYLATES
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DOI：
10.1021/jo00191a028
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发表时间：
1984-01-01
影响因子：
3.6
通讯作者：
KRUSE, LI
中科院分区：
文献类型：
--
作者：
MEYER, MD;KRUSE, LI
报道了一种新的取代麦角林合成子3，4-二氢-6-甲氧基苯并[cd]吲哚-5（1H）-酮的有效合成方法。一般的合成策略也被应用于制备已知的3，4-二氢苯并[cd]吲哚-5-（1H）-酮，乌勒酮。中间体2-羧基-3，4-二氢苯并[cd]吲哚-5（1H）-酮的脱羧反应是通过将羧酸乙酯还原为吲哚-2-甲醛，然后使用原位生成的Rh（1，3-双（二苯基膦基）丙烷）2+Cl-催化剂催化脱羰基为母体吲哚来完成的。催化脱羰基反应被推广到其他几个吲哚-2-甲醛，似乎是吲哚醛的一般反应。
An efficient synthesis of a new substituted ergoline synthon, 3,4-dihydro-6-methoxybenz[cd]indol-5(1H)-one, is described. The general synthetic strategy was also applied to the preparation of the known 3,4-dihydrobenz[cd]indol-5-(1H)-one, Uhle''s ketone. The key step, a formal decarboxylation of intermediate 2-carboxy-3,4-dihydrobenz[cd]indol-5(1H)-one, is accomplished by reduction of the carboxylate ethyl ester to the indole-2-carboxaldehyde followed by catalytic decarbonylation to the parent indole using in situ generated Rh(1,3-bis(diphenylphosphino)propane)2+Cl- catalyst. The catalytic decarbonylation reaction was extended to several other indole-2-carboxaldehydes and appears to be a general reaction of indole aldehydes.