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A Facile Synthesis of Pechmann Dyes
Author(s) -
Hopf Henning,
Jones Peter G.,
Nicolescu Alina,
Bicu Elena,
Birsa Lucian M.,
Belei Dalila
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201400329
Subject(s) - phenacyl , chemistry , combinatorial chemistry , halide , organic chemistry , coumarin , scope (computer science) , computer science , programming language
A facile synthesis of Pechmann dyes has been accomplished by the reaction of substituted N ‐phenacyl‐4‐dimethylaminopyridinium halides with dimethyl maleate in the presence of DBU. Based on a related 4‐DMAP elimination product and an isolated monolactone intermediate a reaction mechanism has been proposed. The scope of this synthetic method is determined by the availability of α‐haloaroyl or heteroaroyl derivatives. DBU=1,8‐diazabicycloundec‐7‐ene, DMAP=4‐dimethylaminopyridine.