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Zeolite‐promoted Synthesis of Coumarins and Thiocoumarins
Author(s) -
Zaitceva Olesia,
Bénéteau Valérie,
Ryabukhin Dmitry S.,
Louis Benoit,
Vasilyev Aleksander V.,
Pale Patrick
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201901384
Subject(s) - zeolite , molecular sieve , chemistry , intramolecular force , homogeneous , lewis acids and bases , brønsted–lowry acid–base theory , aryl , organic chemistry , yield (engineering) , catalysis , materials science , physics , alkyl , metallurgy , thermodynamics
Acidic zeolites, especially faujasites, efficiently promote the intramolecular cyclization of aryl propynoates and propynethioates, which produces coumarins and thiocoumarins, usually in high yields. Comparison with homogeneous Lewis or BrØnsted acids and with heterogeneous related sieve materials revealed the prevalence of zeolites exhibiting large cage‐type pores (H‐USY) for such cyclizations. Various substituents proved compatible with the cyclization process, leading to a variety of substituted coumarins and thiocoumarins (20 examples, 30–99 %).