Selective substitution reactions of methoxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes with active methylene compounds |
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| Authors: | Liejin Zhou Xin Lv Hui Mao Xiaoxia Wang |
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| Institution: | 1. Zhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Zhejiang Normal University, Jinhua 321004, People's Republic of China;2. College of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, People's Republic of China |
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| Abstract: | Benzotriazole adducts methoxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes 1 were derived from the condensation of an aldehyde, benzotriazole, and methylcarbamate. The leaving tendency of methoxycarbonylamino group (MeOCONH) and benzotriazole group (Bt) was investigated by treatment of the adducts with active methylene compounds under either Lewis acid‐catalyzed or basic conditions. In the presence of SmI3, MeOCONH take priority over Bt in the leaving process, whereas in the presence of MeONa, the Bt was substituted in preference. Thus, the tunable substitution of the two leaving groups could be used for different synthetic purposes. J. Heterocyclic Chem., 00 , 00 (2011). |
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