Synthesis of 2-Substituted 3-Alkylidene-2,3-dihydro-1H-isoindol-1-imines through Cyclization of [1-(2-Cyanophenyl)-alkylidene]aminide Intermediates Generated from the Reaction of 2-(1-Azidoalkyl)benzonitriles with NaH
Synthesis of 2-Substituted 3-Alkylidene-2,3-dihydro-1H-isoindol-1-imines through Cyclization of [1-(2-Cyanophenyl)-alkylidene]aminide Intermediates Generated from the Reaction of 2-(1-Azidoalkyl)benzonitriles with NaH
复制标题
2-(1-叠氮基烷基)反应生成的[1-(2-氰基苯基)-亚烷基]胺中间体环化合成2-取代3-亚烷基-2,3-二氢-1H-异吲哚-1-亚胺
DOI：
10.1002/hlca.201400261
复制
发表时间：
2014
影响因子：
1.8
通讯作者：
Ippei Nozawa
中科院分区：
文献类型：
--
作者：
Kazuhiro Kobayashi;Kosuke Ezaki;Ippei Nozawa
已经开发了用于制备3-亚烷基-2，3-二氢-1H-异吲哚-1-亚胺衍生物6的方便序列。因此，2-（1-叠氮基烷基）苯甲腈2（容易从2-烷基苯甲腈获得）与NaH在DMF中在0°至室温下反应，生成[1-（2-氰基苯基）亚烷基]酰胺中间体3，其环化和随后的重排，随后用烷基卤化物烷基化，以通常中等的产率得到2-取代的1-亚烷基-2，3-二氢-1H-异吲哚-2-亚胺6。
A convenient sequence for the preparation of 3‐alkylidene‐2,3‐dihydro‐1H‐isoindol‐1‐imine derivatives6has been developed. Thus, 2‐(1‐azidoalkyl)benzonitriles2, readily accessible from 2‐alkylbenzonitriles, are allowed to react with NaH in DMF at 0° to room temperature to generate [1‐(2‐cyanophenyl)alkylidene]aminide intermediates3, of which cyclization and the subsequent rearrangement, followed by alkylation with alkyl halides, affords 2‐substituted 1‐alkylidene‐2,3‐dihydro‐1H‐isoindol‐2‐imines6in generally moderate yields.