Preparation of the isomeric azaindoline family by intramolecular carbolithiation
Preparation of the isomeric azaindoline family by intramolecular carbolithiation
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DOI：
10.1021/ol702862d
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发表时间：
2008-03-20
期刊：
影响因子：
5.2
通讯作者：
Sharma, Vijayata
中科院分区：
文献类型：
--
作者：
Bailey, William F.;Salgaonkar, Paresh D.;Sharma, Vijayata
已经开发了一种操作方便的一锅三步序列，其通过由适当的(N，N-二烯丙基氨基)溴吡啶衍生的芳基锂的分子内碳化反应来获得3-取代的4-，5-，6-和7-氮杂多林(2，3-二氢-1H-吡啶)。在3-CH(2)Li基质子化后环化得到1-烯丙基-3-甲基-4-氮杂环己烷和1-烯丙基-3-甲基-6-氮杂环己烷，而3-甲基-5-氮杂环己烷和3-甲基-7-氮杂环己烷的异构体在用甲醇猝灭之前生成3-甲基-N-烯丙基阴离子。
An operationally convenient, one-pot, three-step sequence has been developed that provides access to 3-substituted 4-, 5-, 6-, and 7-azaindolines (2,3-dihydro-1H-pyrollopyridines) via intramolecular carbolithiation of the aryllithium derived from an appropriate (N,N-diallylamino)bromopyridine. Whereas cyclization proceeds as expected to give 1-allyl-3-methyl-4-azaindoline and 1-allyl-3-methyl-6-azaindoline following protonation of the 3-CH(2)Li group of the azaindoline, the isomeric 3-methyl-5-azaindoline and 3-methyl-7-azaindoline are generated as 3-methyl-N-allyl anions prior to quench with MeOH.