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Title: Rearrangement of imine double bond in activated quinazolinones: Synthesis of phaitanthrin E
Authors: Vaidya, Sagar D
Argade, Narshinha P
Keywords: Tryptanthrin;Wolff-Kishner reduction;Indoloquinazolinone;Base;Acylation;Prototropic shift;Phaitanthrin E and analogues
Issue Date: May-2017
Publisher: NISCAIR-CSIR, India
Abstract: Wolff-Kishner reduction of tryptanthrin to indoloquinazolinone followed by lithium diisorpropylamide induced acylation of the active methylene group with methyl chloroformate directly furnishes the phaitanthrin E in very good yield. Similar acylations of indoloquinazolinone have also been performed with four different acyl chlorides. In all examples, facile rearrangement of imine double bond from quinazolinone to indole moiety to form the corresponding α,β-unsaturated carbonyl system is observed.
Page(s): 527-530
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.56B(05) [May 2017]

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