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Synthesis of 2‐Substituted 3‐Alkylidene‐2,3‐dihydro‐1 H ‐isoindol‐1‐imines through Cyclization of [1‐(2‐Cyanophenyl)alkylidene]aminide Intermediates Generated from the Reaction of 2‐(1‐Azidoalkyl)benzonitriles with NaH
Author(s) -
Kobayashi Kazuhiro,
Ezaki Kosuke,
Nozawa Ippei
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201400261
Subject(s) - chemistry , halide , medicinal chemistry , imine , alkylation , alkyl , organic chemistry , catalysis
Abstract A convenient sequence for the preparation of 3‐alkylidene‐2,3‐dihydro‐1 H ‐isoindol‐1‐imine derivatives 6 has been developed. Thus, 2‐(1‐azidoalkyl)benzonitriles 2 , 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 intermediates 3 , of which cyclization and the subsequent rearrangement, followed by alkylation with alkyl halides, affords 2‐substituted 1‐alkylidene‐2,3‐dihydro‐1 H ‐isoindol‐2‐imines 6 in generally moderate yields.