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Quinazolinone derivatives. Kinetics of the reaction of 2‐chloromethyl‐3‐hydroxy‐4‐(3 H )quinazolinone with nucleophiles
Author(s) -
Fernandez Beatriz M.,
Schapira Celia B.,
Lamdan Samuel
Publication year - 1980
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.5570170409
Subject(s) - quinazolinone , chemistry , nucleophile , dimer , medicinal chemistry , kinetics , hydroxide , reaction rate constant , organic chemistry , catalysis , physics , quantum mechanics
Reaction of 2‐Chloromethyl‐3‐hydroxy‐4(3 H )quinazolinone ( 1 ) with aliphatic amines and hydroxide follows two different routes affording substituted methyl quinazolinones and a dimer 2 derived from 1 . The former were formed by S N 2 reactions while the latter was formed by an inter‐molecular nucleophilic displacement. Second‐order and third‐order rate constants, respectively, were determined, and the kinetic factors influencing both parallel reactions were analysed.