regiospecific approach to 2- and 2,3-disubstituted indole derivatives in high yields via a one-pot aromatization driven dehydration pathway. This method allows a convenient preparation of diallyl indoles that are used as ring-closing metathesis (RCM) precursors for the orthogonal synthesis of pyrido[1,2-a]indoles and carbazoles. The synthetic utility of this method is illustrated by the synthesis of a microtubulin
以前未开发的将格利雅(Grignard)添加到羟吲哚中的方法通过一锅芳构化驱动的脱水途径,以高收率提供了一种区域特异性的方法,用于2-和2,3-二取代的吲哚衍生物。这种方法可以方便地制备用作烯丙基[1,2- a ]吲哚和咔唑的正交合成的闭环复分解(RCM)前体的二烯丙基吲哚。该方法的合成效用通过微管蛋白抑制剂和天然存在的咔唑生物碱的合成来说明。
FLASH VACUUM PYROLYSIS OF 2-BENZYLPYRIDINE<i>N</i>-OXIDES. SYNTHESIS OF METHYLPYRIDO[1,2-<i>a</i>]INDOLES
作者:Akio Ohsawa、Takayuki Kawaguchi、Hiroshi Igeta
DOI:10.1246/cl.1981.1737
日期:1981.12.5
Flashvacuumpyrolysis of 2-benzylpyridine N-oxides afforded pyrido[1,2-a]-indole and its various methyl-substituted derivatives in moderate yields. Benzo[g]quinoline in the pyrolyses of 2-(o-methylbenzyl)pyridine N-oxide and 2-benzyl-3-methylpyridine Noxide, and 2-(β-styryl)pyridine in the reaction of 2-(β-phenethyl)pyridine N-oxide were major products as exceptional cases.