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A facile synthesis of 2-substituted indoles from (2-aminobenzyl)triphenylphosphonium salts

✍ Scribed by Shin'ichi Taira; Hiroshi Danjo; Tsuneo Imamoto


Book ID
104250882
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
95 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


A variety of 2-substituted 1-acylindoles were obtained in yields ranging from 40 to 94% by intramolecular Wittig reaction employing (2-aminobenzyl)triphenylphosphonium derivatives and acid anhydride in the presence of triethylamine. The reaction of (2-aminobenzyl)phosphonium derivatives with various acyl chlorides in 2,6-lutidine also proceeded to give the corresponding indoles in 28-67% yields.


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Dedicated to GCnnther Ohhff (1 6.X11.92) Halogenation of Et3N, (i-Pr),EtN, and N-ethylmorpholine or of enamines with dichlorotriphenylphosphorane gives in up to 75 % yield the corresponding [2-(dialkylamino)vinyl]tr1phenylphosphonium chlorides, which can be readily converted into the corresponding s