Intramolecular nucleophilic substitution at an sp 2 carbon: synthesis of substituted thiazoles and imidazole-2-thiones

…, YX Wong, ML Tong, PLY Teo, S Chiba, K Narasaka

Index: Shen, Shu-Su; Lei, Mao-Yi; Wong, Yun-Xuan; Tong, Mun-Ling; Teo, Priscilla Lu-Yi; Chiba, Shunsuke; Narasaka, Koichi Tetrahedron Letters, 2009 , vol. 50, # 26 p. 3161 - 3163

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Citation Number: 14

Abstract

Concerted nucleophilic substitution reactions at sp 3 atoms are commonly encountered in mechanistic and synthetic organic chemistry. Although such a substitution reaction at a vinylic sp 2 carbon of unactivated vinyl halides rarely occurs, some examples were reported recently. For examples, 2-bromoallylamines were cyclized to aziridines by base treatment, and the stereospecificity of the cyclization reaction suggested that amino group approached from the backside of ...