Commercial Zinc Oxide: A Facile, Efficient, and Eco-friendly Catalyst for the One-Pot Three-Component Synthesis of Multisubstituted 2‑Aminothiophenes via the Gewald Reaction

Commercial Zinc Oxide: A Facile, Efficient, and Eco-friendly Catalyst for the One-Pot Three-Component Synthesis of Multisubstituted 2‑Aminothiophenes via the Gewald Reaction

An eco-friendly, simple, and effective protocol is developed for the synthesis of various multisubstituted 2-aminothiophenes. In the presence of a catalytic amount of ZnO (5 mol %), ketones or aldehydes, malononitrile and elemental sulfur were converted to the corresponding 2-aminothiophene derivati...

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Bibliographic Details
Published in:Industrial & engineering chemistry research Vol. 51; no. 44; pp. 14577 - 14582
Main Authors: Tayebee, Reza, Ahmadi, S. Javad, Rezaei Seresht, Esmaeil, Javadi, Farzad, Yasemi, Mohammad A, Hosseinpour, Morteza, Maleki, Behrouz
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 07-11-2012
Subjects:
Applied sciences
Catalysis
Catalysts
Catalytic activity
Catalytic reactions
Chemical engineering
Chemistry
Derivatives
Exact sciences and technology
General and physical chemistry
Industrial engineering
Ketones
Reactors
Sulfur
Synthesis
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Zinc oxide
Catalyst
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Summary:An eco-friendly, simple, and effective protocol is developed for the synthesis of various multisubstituted 2-aminothiophenes. In the presence of a catalytic amount of ZnO (5 mol %), ketones or aldehydes, malononitrile and elemental sulfur were converted to the corresponding 2-aminothiophene derivatives in moderate to high yields (27%–70%) under solvent-free conditions at 100 °C. Zinc oxide as an efficient, readily available, and reusable catalyst, showed very good catalytic activity for the synthesis of 2-aminothiophene derivatives. Thus far, little research has been reported on the Gewald reaction under solvent-free conditions; to the best of our knowledge, this is the first time that it has been proposed as an inexpensive and readily available catalyst for use in the target synthetic route.
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ISSN:0888-5885
1520-5045
DOI:10.1021/ie301737h