SUCCESSFUL THERMAL REARRANGEMENTS OF ACRYLENAMIDES TO GIVE TETRAHYDRO-2-PYRIDONES UNDER FVT CONDITIONS
作者： Stanislaw Lesniak , Beata Pasternak
关键词: Chemistry 、 Computational chemistry 、 Flash (photography) 、 Thermal decomposition 、 Thermal 、 Organic chemistry
摘要: ABSTRACT Enamides of α,β-unsaturated acids are theoretically capable electrocyclisation to give tetrahydro-2-pyridones. The only successful method reported for this conversion involved photochemical activation. We would like present new and effective transformation using flash vacuum thermolysis.
sci-hub.se 参考文章(11)
R. Shabana, J.B. Rasmussen, S.O. Olesen, S.-O. Lawesson, Imine chemistry—II: A new route to cyclic enaminones from imines and β-propiolactone or α,β-unsatu rated acids the preparation of enamino-thiones Tetrahedron. ,vol. 36, pp. 3047- 3051 ,(1980) , 10.1016/0040-4020(80)88031-8
Masami Sakamoto, Tohru Yanase, Tsutomu Fujita, Shoji Watanabe, Hiromu Aoyama, Yoshimori Omote, Thietane-fused β-lactams via photochemical cycloaddition reaction of N-(α, β-unsaturated carbonyl)thioamides Journal of The Chemical Society-perkin Transactions 1. pp. 403- 407 ,(1991) , 10.1039/P19910000403
K. Paulvannan, John R. Stille, Formation of 1,2,3,4-tetrahydro-2-pyridones by aza-annulation of imines with acrylate derivatives Journal of Organic Chemistry. ,vol. 57, pp. 5319- 5328 ,(1992) , 10.1021/JO00046A011
Rudolf Knorr, Anton Schnegg, Ernst Lattke, Edith Räpple, 1H-Kernresonanzverschiebungen in der Gerüstebene anisotroper CO-, CN- und CC-Doppelbindungen Chemische Berichte. ,vol. 112, pp. 3490- 3514 ,(1979) , 10.1002/CBER.19791121017
K. E. Schulte, I. Mleinek, K. H. Schär, Zur Kenntnis der Acetylencarbonsäuren. IX. Mitteilung: Die Bildung ungesättigter Lactone aus Alkinsäuren Archiv der Pharmazie. ,vol. 291, pp. 227- 237 ,(1958) , 10.1002/ARDP.19582910505
Zen-ichi Horii, Chuzo Iwata, Ichiya Ninomiya, Nobuhiko Imamura, Masayoshi Ito, Yasumitsu Tamura, Studies on Ergot Alkaloids and Its Related Compounds. X. Condensation of Cyclic Ketones and 3-Methylaminopropionates Chemical & Pharmaceutical Bulletin. ,vol. 12, pp. 1405- 1415 ,(1964) , 10.1248/CPB.12.1405
Kevin T. Potts, Thevarak Rochanapruk, Albert Padwa, Steven J. Coats, Lazaros Hadjiarapoglou, Intramolecular 1,4-Dipolar Cycloadditions of Cross-Conjugated Heteroaromatic Betaines. Synthesis of Hexahydrojulolidines and Related Peri- and Ortho-Fused Ring Systems Journal of Organic Chemistry. ,vol. 60, pp. 3795- 3805 ,(1995) , 10.1021/JO00117A035
Agustin Cobas, Enrique Guitian, Luis Castedo, Synthesis of 3-phenylisoquinolones by reaction of simple pyrroline-2,3-diones with benzyne. New mechanistic considerations Journal of Organic Chemistry. ,vol. 58, pp. 3113- 3117 ,(1993) , 10.1021/JO00063A034
Matthew S. Sell, Walter R. Klein, Reuben D. Rieke, A Facile Synthesis of .gamma.-Lactams and Secondary Amines from Conjugated Dienes and Imines Journal of Organic Chemistry. ,vol. 60, pp. 1077- 1080 ,(1995) , 10.1021/JO00109A048
Albert Padwa, Steven J. Coats, Lazaros Hadjiarapoglou, 8H-ANHYDRO-4-HYDROXY-2-OXO-1,3-THIAZINIUM HYDROXIDES AS MESOIONIC 1,4-DIPOLES Heterocycles. ,vol. 41, pp. 1631- 1652 ,(1994) , 10.3987/COM-93-S(B)16-1