Synthesis of 1‐(benzotriazol‐1‐yl)alkyldiphenylphosphine oxides and their transformations to novel benzotriazol‐1‐yl‐substituted cyclopropanes | Zendy

Katritzky Alan R. | Zendy; Wu Hong | Zendy; Xie Linghong | Zendy; Jiang Jinlong | Zendy

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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.

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