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Selective substitution reactions of methoxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes with active methylene compounds
Author(s) -
Zhou Liejin,
Lv Xin,
Mao Hui,
Wang Xiaoxia
Publication year - 2011
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.612
Subject(s) - chemistry , benzotriazole , methylene , adduct , leaving group , lewis acids and bases , aldehyde , medicinal chemistry , organic chemistry , stereochemistry , catalysis
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).