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Construction of Diverse and Functionalized 2 H ‐Chromenes by Organocatalytic Multicomponent Reactions
Author(s) -
Cai Hongyun,
Xia Likai,
Lee Yong Rok,
Shim JaeJin,
Kim Sung Hong
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500616
Subject(s) - chemistry , salicylaldehyde , regioselectivity , green chemistry , organic chemistry , organocatalysis , combinatorial chemistry , quinoline , catalysis , reaction conditions , reaction mechanism , stereochemistry , enantioselective synthesis , schiff base
A green and efficient one‐pot process for the construction of diverse and functionalized 2 H ‐chromenes was developed by using multicomponent reactions of salicylaldehydes, alkynes (i.e., propiolate and acetylenedicarboxylates), and alcohols. This new protocol was achieved by using L ‐proline as a mild and green organocatalyst and offers several advantages such as economic availability, low toxicity, ease of handling, high regioselectivity, and environmentally benign nature under mild reaction conditions. As an extension of this method, quinoline derivatives were synthesized by replacing salicylaldehyde with 2‐aminobenzaldehyde, and the 2‐hydroxy‐2 H ‐chromenes prepared by this approach were also successfully transformed into biologically interesting coumarins through an oxidation reaction.