Synthesis of 8-Substituted Xanthines and Their Oxidative Skeleton Rearrangement to 1-Oxo-2,4,7,9-tetraazaspiro[4,5]dec-2-ene-6,8,10-triones
1999; Wiley; Volume: 1999; Issue: 9 Linguagem: Inglês
10.1002/(sici)1099-0690(199909)1999
ISSN1434-193X
AutoresH. Zimmer, Adel Amer, Frank Baumann, Michael Haecker, Christopher G. M. Hess, Douglas M. Ho, Hans J. Huber, Klaus R. Koch, K. Mahnke, Christian Schumacher, Robert C. Wingfield,
Tópico(s)Porphyrin and Phthalocyanine Chemistry
ResumoEuropean Journal of Organic ChemistryVolume 1999, Issue 9 p. 2419-2428 Full Paper Synthesis of 8-Substituted Xanthines and Their Oxidative Skeleton Rearrangement to 1-Oxo-2,4,7,9-tetraazaspiro[4,5]dec-2-ene-6,8,10-triones Hans Zimmer, Hans Zimmer [email protected] Search for more papers by this authorAdel Amer, Adel Amer [email protected] Department of Chemistry, Faculty of Science, United Arab Emirates University, P.O. Box 17551, Al Ain, UAE Fax: (internat.) + 971-3/671291Search for more papers by this authorFrank M. Baumann, Frank M. Baumann Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorMichael Haecker, Michael Haecker Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorChristopher G. M. Hess, Christopher G. M. Hess Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorDouglas Ho, Douglas Ho Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorHans J. Huber, Hans J. Huber Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorKlaus Koch, Klaus Koch Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorK. Mahnke, K. Mahnke Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorChristian Schumacher, Christian Schumacher Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorRobert C. Wingfield, Robert C. Wingfield Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this author Hans Zimmer, Hans Zimmer [email protected] Search for more papers by this authorAdel Amer, Adel Amer [email protected] Department of Chemistry, Faculty of Science, United Arab Emirates University, P.O. Box 17551, Al Ain, UAE Fax: (internat.) + 971-3/671291Search for more papers by this authorFrank M. Baumann, Frank M. Baumann Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorMichael Haecker, Michael Haecker Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorChristopher G. M. Hess, Christopher G. M. Hess Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorDouglas Ho, Douglas Ho Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorHans J. Huber, Hans J. Huber Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorKlaus Koch, Klaus Koch Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorK. Mahnke, K. Mahnke Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorChristian Schumacher, Christian Schumacher Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this authorRobert C. Wingfield, Robert C. Wingfield Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA Fax: (internat.) + 1-513/556-9239Search for more papers by this author First published: 12 August 1999 https://doi.org/10.1002/(SICI)1099-0690(199909)1999:9 3.0.CO;2-1Citations: 6AboutPDF 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 The synthesis of a number of 8-(dialkylamino)- and 8-alkoxyxanthines (3 and 6, respectively) is described. Treatment of 3 with m-chloroperoxybenzoic acid (m-CPBA) gave by a novel rearrangement 3-(disubstituted amino)-4,7,9-trimethyl-1-oxo-2,4,7,9-tetraazaspiro[4,5]dec-2-ene-6,8,10-triones 10. Also, the corresponding 3-alkoxy-subtituted spiro compounds 12 were obtained by an analogus treatment of 8-alkoxyxanthines 6. In attempts to elucidate a tentative mechanism for this rearrangement 8-[(dialkylamino)methyl]caffeines 7 when treated with m-CPBA did not undergo the rearrangement but only yielded the expected N-oxide derivatives 16. This result seems to indicate that a necessary structure element for this rearrangement to occur is an atom with an unshared pair of electrons to be attached to the 8-position of the investigated xanthines. In agreement with this statement is the fact that N-oxides of 8-[(dialkylamino)methyl]caffeines 16 do not undergo the novel rearrangement but rather give the expected Meisenheimer rearrangement or the Cope elimination depending upon reaction conditions. 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