Access to 2‐Amino‐3‐Arylthiophenes by Base‐Catalyzed Redox Condensation Reaction Between Arylacetonitriles, Chalcones, and Elemental Sulfur

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...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-01, Vol.362 (1), p.160-165
Main Authors: Nguyen, Thi Thu Tram, Le, Van Anh, Retailleau, Pascal, Nguyen, Thanh Binh
Format: Article
Language:English
Subjects:
2-aminothiophene
Aromatic compounds
arylacetonitrile
Catalysis
chalcone
Chemical Sciences
Organic chemistry
oxidative sulfuration
Substrates
Sulfur
Thiophenes
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201901235