Furan ring opening - isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes
2006; Wiley; Volume: 43; Issue: 5 Linguagem: Inglês
10.1002/jhet.5570430510
ISSN1943-5193
AutoresВладимир Т. Абаев, Artem S. Dmitriev, Sergey A. Podelyakin, А. В. Бутин, Andrey Gutnov,
Tópico(s)Marine Sponges and Natural Products
ResumoJournal of Heterocyclic ChemistryVolume 43, Issue 5 p. 1195-1204 Article Furan ring opening — isocoumarine ring closure: A recyclization reaction of 2-carboxyaryldifurylmethanes Vladimir T. Abaev, Vladimir T. Abaev North-Ossetian State University, Vatutina 46, Vladikavkaz, 362025, RussiaSearch for more papers by this authorArtem S. Dmitriev, Artem S. Dmitriev Kuban State University of Technology, Moskovskaya 2, Krasnodar, 350072, RussiaSearch for more papers by this authorSergey A. Podelyakin, Sergey A. Podelyakin Kuban State University of Technology, Moskovskaya 2, Krasnodar, 350072, RussiaSearch for more papers by this authorAlexander V. Butin, Alexander V. Butin alexander_butin@mail.ru Kuban State University of Technology, Moskovskaya 2, Krasnodar, 350072, RussiaSearch for more papers by this authorAndrey V. Gutnov, Andrey V. Gutnov Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V., Albert-Einstein-Str. 29a 18059 Rostock, GermanySearch for more papers by this author Vladimir T. Abaev, Vladimir T. Abaev North-Ossetian State University, Vatutina 46, Vladikavkaz, 362025, RussiaSearch for more papers by this authorArtem S. Dmitriev, Artem S. Dmitriev Kuban State University of Technology, Moskovskaya 2, Krasnodar, 350072, RussiaSearch for more papers by this authorSergey A. Podelyakin, Sergey A. Podelyakin Kuban State University of Technology, Moskovskaya 2, Krasnodar, 350072, RussiaSearch for more papers by this authorAlexander V. Butin, Alexander V. Butin alexander_butin@mail.ru Kuban State University of Technology, Moskovskaya 2, Krasnodar, 350072, RussiaSearch for more papers by this authorAndrey V. Gutnov, Andrey V. Gutnov Leibniz-Institut für Organische Katalyse an der Universität Rostock e.V., Albert-Einstein-Str. 29a 18059 Rostock, GermanySearch for more papers by this author First published: 13 March 2009 https://doi.org/10.1002/jhet.5570430510Citations: 20AboutPDF 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 A general method for the synthesis of isocoumarine derivatives has been developed. Bis(5-R-2-furyl)methylbenzoic acids (R = methyl, ethyl) underwent recyclization and subsequent cyclization into tetracyclic isochromene-1-one derivatives under treatment with hydrogen chloride in methanol. It has been shown that intermediate 4-(5-R-furan-2-yl)-3-(3-oxo-3-R-propyl)-isochromene-1-ones can be obtained selectively by varying a concentration of the hydrogen chloride and reaction times. In the case of R = tert-butyl only corresponding 4-[5-(tert-butyl)-2-furyl]-3-(4,4-dimethyl-3-oxopentyl)-1-isochromenones were isolated regardless of the reaction conditions. Citing Literature Volume43, Issue5September/October 2006Pages 1195-1204 RelatedInformation
Referência(s)