N-trimethylsilylpyrroles as dienes in the synthesis of 1,4-dihydronaphthalen-1,4-imines and isoindoles†
N-trimethylsilylpyrroles as dienes in the synthesis of 1,4-dihydronaphthalen-1,4-imines and isoindoles†
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N-三甲基硅基吡咯作为二烯用于合成 1,4-二氢萘-1,4-亚胺和异吲哚†
DOI：
10.1002/jhet.5570140209
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发表时间：
1977
影响因子：
2.4
通讯作者：
C. S. Ponticello
中科院分区：
文献类型：
--
作者：
P. Anderson;M. Christy;E. Engelhardt;G. F. Lundell;C. S. Ponticello
本文介绍了由苯炔与N-三甲基硅基吡咯的Diels-Alder加成反应合成1，4-二氢萘-1，4-亚胺的一种简便、通用的方法。N-三甲基硅烷基保护基保护产物免受二次苯炔反应的影响，并且很容易去除。说明了使用1，3-偶极试剂通过逆Diels-桤木序列将1，4-二氢萘-1，4-亚胺转化为异吲哚。
A convenient, general synthetic method for 1,4-dihydronaphthaIen-1,4-imines via the Diels-Alder addition of benzyne to N-trimethylsilylpyrrole is described. The N-trimethylsilyl protecting group protected the product from secondary benzyne reactions and was easily removed. The use of a 1,3-dipolar reagent to convert 1,4-dihydronaphthalen-1,4-imines to isoindoles via a retro-Diels-Alder sequence is illustrated.