Tandem in situ Generation of Azomethine Ylides and Base Sensitive Nitroethylene Dipolarophiles
作者： Imre Fejes , László Tőke , Miklós Nyerges , Chwang Siek Pak
DOI: 10.1016/S0040-4020(99)01028-5
关键词: Pyrrolidine 、 Triethylamine 、 Tandem 、 Base (chemistry) 、 Azomethine ylide 、 Polymer chemistry 、 Chemistry 、 In situ 、 Nitroethylene
摘要: Abstract We have studied the behaviour of 2-acetoxy-nitroethane derivatives in presence triethylamine and an azomethine ylide generated also by action this base same reaction mixture. Under these conditions nitro-olefins are react situ with corresponding dipoles, giving pyrrolidine moderate to good yields.
elsevier.com
sci-hub.se 参考文章(36)
Heinrich Wieland, Euklid Sakellarios, Zur Kenntnis des Nitro‐äthylens European Journal of Inorganic Chemistry. ,vol. 52, pp. 898- 904 ,(1919) , 10.1002/CBER.19190520506
Zoltán Bende, László Töke, Lutz Weber, Gábor Tóth, Frank Janke, Gábor Csonka, 1,3-Dipolare cycloadditionen von 6,7-dialkoxy-3,4-dihydroisochinolinium-Salzen Tetrahedron. ,vol. 40, pp. 369- 375 ,(1984) , 10.1016/S0040-4020(01)91183-4
Miklós Nyerges, 2-Oxoindolin-3-ylidene derivatives as 2π components in 1,3-dipolar cycloadditions of azomethine ylides Synlett. ,vol. 1999, pp. 111- 113 ,(1999) , 10.1055/S-1999-2525
D. Ranganathan, S. Ranganathan, S. Bamezai, Nitroethylene nitroethylation of amines Tetrahedron Letters. ,vol. 23, pp. 2789- 2792 ,(1982) , 10.1016/S0040-4039(00)87459-6
NATHAN L. DRAKE, CHARLOTTE M. KRAEBEL, Polycyclic Compounds Containing Nitrogen. III. The Diels-Alder Reaction of Nitroethylene Journal of Organic Chemistry. ,vol. 26, pp. 41- 45 ,(1961) , 10.1021/JO01060A008
Albert Padwa, Lubor Fisera, Konrad F. Koehler, Augusto Rodriguez, George S. K. Wong, Regioselectivity associated with the 1,3-dipolar cycloaddition of nitrones with electron-deficient dipolarophiles Journal of Organic Chemistry. ,vol. 49, pp. 276- 281 ,(1984) , 10.1021/JO00176A012
S Ranganathan, D Ranganathan, S.K Singh, A practical and convenient synthesis of the nitroethylene transfer reagent, 2-nitroethyl phenyl sulfoxide Tetrahedron Letters. ,vol. 28, pp. 2893- 2894 ,(1987) , 10.1016/S0040-4039(00)96237-3
H. Feuer, A. Hirschfeld, E.D. Bergmann, The Michael reaction of enamines with nitroolefins Tetrahedron. ,vol. 24, pp. 1187- 1192 ,(1968) , 10.1016/0040-4020(68)88066-4
Paul W. Groundwater, Toqir Sharif, Andrea Arany, David E. Hibbs, Michael B. Hursthouse, Ian Garnett, Miklós Nyerges, A novel synthesis of didehydroamino acid esters from azomethine ylides Journal of The Chemical Society-perkin Transactions 1. pp. 2837- 2846 ,(1998) , 10.1039/A803695K
Ralph Kaplan, Harold Shechter, Notes. Generation of Nitroethylene in Situ for Use in Diels-Alder Reactions Journal of Organic Chemistry. ,vol. 26, pp. 982- 983 ,(1961) , 10.1021/JO01062A630