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
2002; Wiley; Volume: 2002; Issue: 20 Linguagem: Inglês
10.1002/1099-0690(200210)2002
ISSN1434-193X
AutoresFabien Cochard, Marie Laronze, Élise Prost, Jean‐Marc Nuzillard, Franck Augé, Christian Petermann, Philippe Sigaut, János Sápi, Jean‐Yves Laronze,
Tópico(s)Multicomponent Synthesis of Heterocycles
ResumoEuropean Journal of Organic ChemistryVolume 2002, Issue 20 p. 3481-3490 Full Paper 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 Fabien Cochard, Fabien Cochard UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorMarie Laronze, Marie Laronze UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorÉlise Prost, Élise Prost UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorJean-Marc Nuzillard, Jean-Marc Nuzillard UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorFranck Augé, Franck Augé UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorChristian Petermann, Christian Petermann UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorPhilippe Sigaut, Philippe Sigaut UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorJanos Sapi, Janos Sapi UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorJean-Yves Laronze, Jean-Yves Laronze jy.laronze@univ-reims.fr UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this author Fabien Cochard, Fabien Cochard UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorMarie Laronze, Marie Laronze UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorÉlise Prost, Élise Prost UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorJean-Marc Nuzillard, Jean-Marc Nuzillard UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorFranck Augé, Franck Augé UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorChristian Petermann, Christian Petermann UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorPhilippe Sigaut, Philippe Sigaut UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorJanos Sapi, Janos Sapi UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this authorJean-Yves Laronze, Jean-Yves Laronze jy.laronze@univ-reims.fr UMR 6013 “Isolement, Structure, Transformations et Synthèse de Produits Naturels”, IFR 53 Biomolécules, Faculté de Pharmacie, Université de Reims Champagne-Ardenne, 51, rue Cognacq-Jay, 51096 Reims cedex, France, Fax: (internat.) +33−326918025Search for more papers by this author First published: 30 September 2002 https://doi.org/10.1002/1099-0690(200210)2002:20 3.0.CO;2-CCitations: 20Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Abstract 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) Citing Literature Volume2002, Issue20October 2002Pages 3481-3490 RelatedInformation
Referência(s)