Remarkable effect of CF 3 CH 2 OH for the halogen induced oxidative rearrangement reaction of aminals leading to 3, 4-dihydroquinazolines

…, M Shimura, R Nagao, D Endo, H Fujioka

Index: Murai, Kenichi; Shimura, Masato; Nagao, Ryu; Endo, Daisuke; Fujioka, Hiromichi Organic and Biomolecular Chemistry, 2013 , vol. 11, # 16 p. 2648 - 2651

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Citation Number: 7

Abstract

The drastic effect of CF 3 CH 2 OH in promoting the rearrangement of the reaction of the N-chloro-derivative of 1a is interesting. Although, to the best of our knowledge, there is no report on the reaction of halo-amines and N-chloro-aminals in CF 3 CH 2 OH, we postulate that the observed efficiency enhancement is a consequence of the highly polar and low nucleophilic properties of this fluorinated alcohol, which could aid in facilitating the N–Cl bond ...