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Hetero‐ Cope ‐Umlagerungen. 4. Mitteilung . Regiokontrollierte Indolsynthesen
Author(s) -
Blechert Siegfried
Publication year - 1985
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.19850680705
Subject(s) - chemistry , deprotonation , cope rearrangement , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , ion , financial economics , economics
Hetero‐ Cope ‐Rearrangements, Regio‐Controlled Synthesis of Indoles The reaction of O ‐deprotonated N ‐phenylhydroxylamines 1 with various electron‐deficient allenes 2 , 14 , 16 gives, via Michael addition and Cope ‐rearrangement, substituted anilines 5 , which are easily convertible into indoles 6 . In this manner, sulfoxides 17 , serve as equivalents of 2‐vinylindoles. Diels ‐ Alder reaction with this 2‐vinylindole equivalent followed by indolisation affords isoquinuclidine derivative 21 which may be a useful precursor for the preparation of Iboga alkaloids.