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Synthesis of Substituted 1,2,3,4‐Tetrahydro‐1‐thiacarbazole and Spiro[pyrrolidinone‐3,3′‐indolinones] through a Common Intermediate Obtained by Condensation of Indolin‐2‐one, (Aryl)aldehydes, and Meldrum's Acid
Author(s) -
Cochard Fabien,
Laronze Marie,
Prost Élise,
Nuzillard JeanMarc,
Augé Franck,
Petermann Christian,
Sigaut Philippe,
Sapi Janos,
Laronze JeanYves
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200210)2002:20<3481::aid-ejoc3481>3.0.co;2-c
Subject(s) - chemistry , condensation , aryl , medicinal chemistry , meldrum's acid , organic chemistry , thermodynamics , alkyl , physics
Trimolecular adducts resulting from condensation between indolin‐2‐one (or indoline‐2‐thione), (aryl)aldehydes, and Meldrum’s acid are useful intermediates for the synthesis of either 1,2,3,4‐tetrahydro‐1‐thiacarbazoles or spiro[pyrrolidino‐3,3′‐oxindoles] related to the natural product horsfiline. These latter compounds were obtained in a three‐step procedure characterized by acyl azide formation, Curtius rearrangement, and subsequent thermal spiro cyclization. The relative stereochemistry of the spiro derivatives was determined by comparison of NOESY data and calculated conformational analyses. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)