Diels-Alder reactions of fused pyran-2-ones with maleimides: efficient syntheses of benz[e]isoindoles and related systems.
作者： Krištof Kranjc , Slovenko Polanc , Marijan Kočevar
DOI: 10.1021/OL034852Q
关键词:
摘要: The Diels−Alder reaction of some substituted 5,6,7,8-tetrahydro-2H-1-benzopyran-2-ones (1a−f) with N-substituted maleimides (2a−c) leading to fused isoindole derivatives (5a−n, 7) or, in a few cases, bridged double cycloadducts (fused bicyclo[2.2.2]octene derivatives) (6a−f) is presented. When X = CO, the first efficient, substituent-driven aromatization an intermediary-formed cycloadduct was observed, resulting benz[e]isoindoles (5a−k). same type can also be achieved unprecedented catalysis Rh/C.
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sci-hub.se 参考文章(14)
Kamyar Afarinkia, Victoria Vinader, Todd D. Nelson, Gary H. Posner, Diels-Alder cycloadditions of 2-pyrones and 2-pyridones Tetrahedron. ,vol. 48, pp. 9111- 9171 ,(1992) , 10.1016/S0040-4020(01)85607-6
Pilar Cano, Antonio Echavarren, Pilar Prados, Francisco Farina, Polycyclic hydroxyquinones. 13. A novel synthesis of islandicin and digitopurpone Journal of Organic Chemistry. ,vol. 48, pp. 5373- 5376 ,(1983) , 10.1021/JO00174A047
Kung K. Wang, Sham S. Nikam, Chihmei D. Ho, Regioselective synthesis of trimethylsilyl-substituted α-allenic alcohols via propargylic organoboranes Journal of Organic Chemistry. ,vol. 48, pp. 5376- 5377 ,(1983) , 10.1021/JO00174A048
Miha Tis̈ler, Vladimir Kepe, Marijan Kocevar, Solvenko Polanc, Bojan Verc̈ek, A simple and general one-pot synthesis of some 2h-pyran-2-ones and fused pyran-2-ones Tetrahedron. ,vol. 46, pp. 2081- 2088 ,(1990) , 10.1016/S0040-4020(01)89774-X
Satoshi Hibino, Eiichi Sugino, Takeshi Kuwada, Naoki Ogura, Kohichi Sato, Tominari Choshi, Synthesis of genotoxic heterocyclic amines Trp-P-1 and Trp-P-2 Journal of Organic Chemistry. ,vol. 57, pp. 5917- 5921 ,(1992) , 10.1021/JO00048A026
Yoh-ichi Matsushita, Kei Sakamoto, Taro Murakami, Takanao Matsui, A Convenient Synthesis of Methyl 4-Substituted Benzoates via Diels-Alder Reaction in the Presence of Palladium on Activated Carbon Synthetic Communications. ,vol. 24, pp. 3307- 3313 ,(1994) , 10.1080/00397919408010254
P. Van Doren, D. Vanderzande, S. Toppet, G. Hoornaert, Diels-alder reactions of pyrano[3,4-b]indol-3-ones with olefinic compounds : Synthesis of (1,2-dihydro)carbazoles Tetrahedron. ,vol. 45, pp. 6761- 6770 ,(1989) , 10.1016/S0040-4020(01)89146-8
A. Baltuška, Th. Udem, M. Uiberacker, M. Hentschel, E. Goulielmakls, Ch. Gohle, R. Holzwarth, V. S. Yakovlev, A. Scrinzi, T. W. Hänsch, F. Krausz, erratum: Attosecond control of electronic processes by intense light fields Nature. ,vol. 422, pp. 189- 189 ,(2003) , 10.1038/NATURE01483
Otto Diels, Kurt Alder, Über die Ursachen der „Azoesterreaktion” Justus Liebig's Annalen der Chemie. ,vol. 450, pp. 237- 254 ,(1926) , 10.1002/JLAC.19264500119
N P Shusherina, Diene Synthesis with 2-Pyrones and 2-Pyridones Russian Chemical Reviews. ,vol. 43, pp. 851- 861 ,(1974) , 10.1070/RC1974V043N10ABEH001867