Electrophilic cyclization of N-alkenylamides using a chloramine-T/I 2 system
…, I Hidaka, Y Oderaotoshi, M Komatsu, S Minakata
Index: Morino, Yoshinobu; Hidaka, Ikumasa; Oderaotoshi, Yoji; Komatsu, Mitsuo; Minakata, Satoshi Tetrahedron, 2006 , vol. 62, # 52 p. 12247 - 12251
Full Text: HTML
Citation Number: 20
Abstract
A new protocol for the cyclization of N-alkenylamides using chloramine-T and iodine is described. When N-alkenylsulfonamides are treated with chloramine-T and iodine, three-to six-membered N-heterocycles are obtained with complete stereoselectivity. The method is compatible with the cyclization of the allylbenzamide or allylbenzthioamide to afford an oxazoline or thiazoline derivative, respectively. Mechanistic studies indicate that the ...
Related Articles:
[Hegedus, Louis S.; McKearin, James M. Journal of the American Chemical Society, 1982 , vol. 104, # 9 p. 2444 - 2451]
IMDAF Cycloaddition as a Method for the Preparation of Pyrrolophenanthridine Alkaloids
[Padwa, Albert; Dimitroff, Martin; Waterson, Alex G.; Wu, Tianhua Journal of Organic Chemistry, 1998 , vol. 63, # 12 p. 3986 - 3997]
[Miura, Katsukiyo; Hondo, Takeshi; Nakagawa, Takahiro; Takahashi, Tatsuyuki; Hosomi, Akira Organic Letters, 2000 , vol. 2, # 3 p. 385 - 388]
A new, simple synthesis of N-tosyl pyrrolidines and piperidines
[Marcotullio, Maria Carla; Campagna, Valerio; Sternativo, Silvia; Costantino, Ferdinande; Curini, Massimo Synthesis, 2006 , # 16 p. 2760 - 2766]
[Feltenberger, John B.; Hayashi, Ryuji; Tang, Yu; Babiash, Eric S.C.; Hsung, Richard P. Organic Letters, 2009 , vol. 11, # 16 p. 3666 - 3669]