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 |
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| Authors: | Kazuhiro Kobayashi Kosuke Ezaki Ippei Nozawa |
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| Institution: | Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4‐101 Koyama‐minami, Tottori 680?–?8552, Japan, (phone/fax: +81‐857‐315263) |
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| Abstract: | A convenient sequence for the preparation of 3‐alkylidene‐2,3‐dihydro‐1H‐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‐1H‐isoindol‐2‐imines 6 in generally moderate yields. |
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| Keywords: | 1H‐Isoindol‐1‐imines 3‐alkylidene‐2 3‐dihydro‐ Benzonitriles 1‐(1‐azidoalkyl)‐ Aminides [1‐(2‐cyanophenyl)alkylidene]‐ Denitrogenation |
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