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Synthesis of 1‐(benzotriazol‐1‐yl)alkyldiphenylphosphine oxides and their transformations to novel benzotriazol‐1‐yl‐substituted cyclopropanes
Author(s) -
Katritzky Alan R.,
Wu Hong,
Xie Linghong,
Jiang Jinlong
Publication year - 1995
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.5570320238
Subject(s) - chemistry , cyclopropane , electrophile , alkylation , yield (engineering) , medicinal chemistry , oxide , organic chemistry , butyllithium , ring (chemistry) , catalysis , materials science , metallurgy
Diphenylphosphinous anion reacted with chloromethylbenzotriazole to give (benzotriazol‐1‐yl)methyldiphenylphosphine oxide, which, after lithiation, was alkylated to give 1‐(benzotriazol‐1‐yl)alkyldiphenylphosphine oxides in good yield. Treatment of 1‐(benzotriazol‐1‐yl)alkyldiphenylphosphine oxides with n ‐butyllithium followed by condensation with epoxides, afforded benzotriazol‐1‐yl‐substituted cyclopropanes, which underwent further lithiation and subsequent reaction with numerous electrophiles to provide a variety of novel benzotriazol‐1‐yl‐substituted cyclopropane derivatives.