Solid-Supported Nitrile Oxides as Stable and Valuable Reactive Intermediates
2002; Wiley; Volume: 2002; Issue: 7 Linguagem: Inglês
10.1002/1099-0690(200204)2002
ISSN1434-193X
AutoresGiuseppe Faita, Mariella Mella, Annalisa Mortoni, Alfredo Paio, Paolo Quadrelli, Pierfausto Seneci,
Tópico(s)Multicomponent Synthesis of Heterocycles
ResumoEuropean Journal of Organic ChemistryVolume 2002, Issue 7 p. 1175-1183 Full Paper Solid-Supported Nitrile Oxides as Stable and Valuable Reactive Intermediates Giuseppe Faita, Giuseppe Faita Dipartimento di Chimica Organica dell’Università degli Studi di Pavia Viale T. Taramelli, 10, 27100 Pavia, ItalySearch for more papers by this authorMariella Mella, Mariella Mella Dipartimento di Chimica Organica dell’Università degli Studi di Pavia Viale T. Taramelli, 10, 27100 Pavia, ItalySearch for more papers by this authorAnnalisa Mortoni, Annalisa Mortoni Dipartimento di Chimica Organica dell’Università degli Studi di Pavia Viale T. Taramelli, 10, 27100 Pavia, ItalySearch for more papers by this authorAlfredo Paio, Alfredo Paio GlaxoSmithKline Group, Glaxo Wellcome Medicines Research Centre, Via A. Fleming 4, 37135 Verona, ItalySearch for more papers by this authorPaolo Quadrelli, Paolo Quadrelli Dipartimento di Chimica Organica dell’Università degli Studi di Pavia Viale T. Taramelli, 10, 27100 Pavia, ItalySearch for more papers by this authorPierfausto Seneci, Pierfausto Seneci Nucleotide Analogue Design, Landsbergerstrasse 50, 80339 München, GermanySearch for more papers by this author Giuseppe Faita, Giuseppe Faita Dipartimento di Chimica Organica dell’Università degli Studi di Pavia Viale T. Taramelli, 10, 27100 Pavia, ItalySearch for more papers by this authorMariella Mella, Mariella Mella Dipartimento di Chimica Organica dell’Università degli Studi di Pavia Viale T. Taramelli, 10, 27100 Pavia, ItalySearch for more papers by this authorAnnalisa Mortoni, Annalisa Mortoni Dipartimento di Chimica Organica dell’Università degli Studi di Pavia Viale T. Taramelli, 10, 27100 Pavia, ItalySearch for more papers by this authorAlfredo Paio, Alfredo Paio GlaxoSmithKline Group, Glaxo Wellcome Medicines Research Centre, Via A. Fleming 4, 37135 Verona, ItalySearch for more papers by this authorPaolo Quadrelli, Paolo Quadrelli Dipartimento di Chimica Organica dell’Università degli Studi di Pavia Viale T. Taramelli, 10, 27100 Pavia, ItalySearch for more papers by this authorPierfausto Seneci, Pierfausto Seneci Nucleotide Analogue Design, Landsbergerstrasse 50, 80339 München, GermanySearch for more papers by this author First published: 07 March 2002 https://doi.org/10.1002/1099-0690(200204)2002:7 3.0.CO;2-ZCitations: 27Read 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 onEmailFacebookTwitterLinkedInRedditWechat Abstract 1,3-Dipolar cycloadditions of Wang resin supported nitrile oxides have been performed with several dipolarophiles to afford 5-membered heterocycles in fair yields. The nitrile oxides displayed increased stability on the solid phase, allowing clean transformations into nitrosocarbonyl intermediates, which could be trapped with suitable dienes to afford hetero Diels−Alder cycloadducts in moderate yields. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002) References 1 For recent reviews see: Google Scholar 1a R. G. Franzen , J. Comb. Chem. 2000 , 2 , 195 −214 . 10.1021/cc000002f CASPubMedWeb of Science®Google Scholar 1b R. E. Dolle , K. H. Nelson , J. Comb. Chem. 1999 , 1 , 235 −282 . 10.1021/cc9900192 CASPubMedWeb of Science®Google Scholar 1c J. H. Van Maarseveen , Comb. Chem. High Throughput Screening 1998 , 1 , 185 −214 . CASPubMedWeb of Science®Google Scholar 1d M. A. Gallop , R. W. 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