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Selective substitution reactions of methoxycarbonylamino-1-(1-benzotriazolyl)alkanes with active methylene compounds

✍ Scribed by Liejin Zhou; Xin Lv; Hui Mao; Xiaoxia Wang

Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
130 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

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 SmI~3~, 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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