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Access to 2‐Amino‐3‐Arylthiophenes by Base‐Catalyzed Redox Condensation Reaction Between Arylacetonitriles, Chalcones, and Elemental Sulfur
Author(s) -
Nguyen Thi Thu Tram,
Le Van Anh,
Retailleau Pascal,
Nguyen Thanh Binh
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201901235
Subject(s) - chemistry , dabco , catalysis , adduct , sulfur , acetonitriles , organic chemistry , redox , methylene , combinatorial chemistry , acetonitrile
A straightforward access to 2‐amino‐3‐arylthiophenes has been developed via one‐pot two‐step three‐component reaction of arylacetonitriles, chalcones and elemental sulfur. The first step consists of a DBU‐catalyzed formation of Michael adduct between arylacetonitriles and chalcones. The second step is a cascade of DABCO‐catalyzed sulfuration of the Michael adduct with elemental sulfur followed by an oxidative cyclization to afford thiophenes. Compared to the Gewald reactions and related transformations which are limited in acetonitriles bearing a methylene group activated by an α‐substituted electron withdrawing group as substrates, our method can be applied to a wide range of arylacetonitriles and requires only catalytic amounts of DBU and DABCO. The developed reaction opens an access to 3‐aryl‐2‐aminothiophenes complementary to classical Gewald reactions with high degree of structural diversity and atom efficiency.