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Regioselective Anionic [3+2] Cyclizations of Isoxazole, Pyrazole and 1,2,4-Triazole Dinucleophiles − Efficient Synthesis of 2,4-Dihydroimidazo[4,5-b]quinoxalines, 3H-Imidazo[1,2-b]pyrazoles and 5H-Imidazo[2,1-c][1,2,4]triazoles

2001; Wiley; Volume: 2001; Issue: 12 Linguagem: Inglês

10.1002/1099-0690(200106)2001

1434-193X

Peter Langer, Jörg Wuckelt, Manfred Döring, Peter R. Schreiner, Helmar Görls,

Synthesis and Characterization of Heterocyclic Compounds

European Journal of Organic ChemistryVolume 2001, Issue 12 p. 2257-2263 Full Paper Regioselective Anionic [3+2] Cyclizations of Isoxazole, Pyrazole and 1,2,4-Triazole Dinucleophiles − Efficient Synthesis of 2,4-Dihydroimidazo[4,5-b]quinoxalines, 3H-Imidazo[1,2-b]pyrazoles and 5H-Imidazo[2,1-c][1,2,4]triazoles Peter Langer, Peter Langer Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, GermanySearch for more papers by this authorJörg Wuckelt, Jörg Wuckelt Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this authorManfred Döring, Manfred Döring Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this authorPeter R. Schreiner, Peter R. Schreiner Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany Department of Chemistry, The University of Georgia, 1001 Cedar St., Athens, GA 30602-2556, USASearch for more papers by this authorHelmar Görls, Helmar Görls Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this author Peter Langer, Peter Langer Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, GermanySearch for more papers by this authorJörg Wuckelt, Jörg Wuckelt Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this authorManfred Döring, Manfred Döring Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this authorPeter R. Schreiner, Peter R. Schreiner Institut für Organische Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany Department of Chemistry, The University of Georgia, 1001 Cedar St., Athens, GA 30602-2556, USASearch for more papers by this authorHelmar Görls, Helmar Görls Institut für Anorganische und Analytische Chemie der Universität Jena, August-Bebel-Strasse 2, 07743 Jena, GermanySearch for more papers by this author First published: 15 May 2001 https://doi.org/10.1002/1099-0690(200106)2001:12 3.0.CO;2-ZCitations: 19Read 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 onFacebookTwitterLinked InRedditWechat Abstract Regioselective cyclization reactions between oxaldiimidoyl dichlorides and 3-aminopyrazole and 3-amino-1,2,4-triazole provide convenient access to biologically relevant 3H-imidazo[1,2-b]pyrazoles and a 5H-imidazo[2,1-c][1,2,4]triazole. In contrast, treatment of 3-aminoisoxazoles with diimidoyl dichlorides results in a new and efficient anionic domino process for the synthesis of biologically relevant 2,4-dihydro-1H-imidazo[4,5-b]quinoxalines. All cyclizations proceed with high regioselectivities, which are explained with the aid of semiempirical computations. Citing Literature Volume2001, Issue12June 2001Pages 2257-2263 RelatedInformation