Synthese von Benzofuranen durch Cyclodehydrierung von Phenylmalonylheterocyclen

作者: Wolfgang Stadlbauer , Otto Schmut , Thomas Kappe

DOI: 10.1007/BF00909657

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摘要: Phenylmalonyl heterocyclic compounds such as the quinolones1a–c or3, benzoquinolizinones6a, b and phenalenones8a, can be converted to benzofuranes (2a–c, 7a, and9a, b) by cyclodehydrogenation with Pd/C in boiling diphenyl ether. 2-Phenylchinchonic acid (10) reacts under same conditions dimeric benzofuroquinoline12: decarboxylated quinoline11 however gives monomer13.

参考文章(15)
Th. Kappe, M. Ali A. Chirazi, H. Peter Stelzel, E. Ziegler, Synthesen von Heterocyclen, 162. Mitt.: Zur Synthese von N-Malonylheterocyclen Monatshefte Fur Chemie. ,vol. 103, pp. 586- 598 ,(1972) , 10.1007/BF00904962
Serge Lang, Linear Theory of Theta Functions Springer, New York, NY. pp. 83- 109 ,(1972) , 10.1007/978-1-4612-5740-0_6
Thomas Kappe, Alexander Brandner, Notizen: Eine einfache Synthese des Cumöstrols / A Simple Synthesis of Coumestrol Zeitschrift für Naturforschung B. ,vol. 29, pp. 292- 293 ,(1974) , 10.1515/ZNB-1974-3-445
Martin Brenner, Charles Brush, The synthesis of substituted benzophenalenofurans a novel pentacyclic ring system Tetrahedron Letters. ,vol. 18, pp. 419- 422 ,(1977) , 10.1016/S0040-4039(01)92654-1
Wolfgang Stadlbauer, Thomas Kappe, Notizen: Eine neue Synthese von β-Brasanchinon / A New Synthesis of β-Brazanquinone Zeitschrift für Naturforschung B. ,vol. 30, pp. 139- 140 ,(1975) , 10.1515/ZNB-1975-1-237
Paul Baumgarten, Walter Kärgel, Über eine Synthese von 2.4‐Dioxy‐chinolinen European Journal of Inorganic Chemistry. ,vol. 60, pp. 832- 842 ,(1927) , 10.1002/CBER.19270600403
Gladys Silverman, Thomas Flynn, R. Ian Fryer, Armin Walser, Nucleophilic displacement of aromatic fluorine, Part III, indoloquinolines and benzofuranoquinolines Journal of Heterocyclic Chemistry. ,vol. 12, pp. 351- 358 ,(1975) , 10.1002/JHET.5570120227
Hanns John, Chinolinderivate, XXXVIII. Synthese 2-phenylierter-3-Oxy-chinolin-4-carbonsäuren Journal Fur Praktische Chemie-chemiker-zeitung. ,vol. 133, pp. 259- 272 ,(1932) , 10.1002/PRAC.19321330902