Synthesis 2018; 50(02): 361-370
DOI: 10.1055/s-0036-1588585
paper
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Simultaneous Activation of C–H and N–H Bonds: Three-Component One-Pot Cascade Synthesis of Multi­substituted Imidazoles

Sachin D. Pardeshi
a  National Centre for Nanosciences and Nanotechnology, University of Mumbai, Vidyanagari, Kalina Campus, Santacruz (East), Mumbai-400098, India   eMail: achaskar25@gmail.com
,
Pratima A. Sathe
a  National Centre for Nanosciences and Nanotechnology, University of Mumbai, Vidyanagari, Kalina Campus, Santacruz (East), Mumbai-400098, India   eMail: achaskar25@gmail.com
,
Kamlesh S. Vadagaonkar
b  Department of Dyestuff Technology, Institute of Chemical Technology, Nathalal Parekh Marg, Matunga (East), Mumbai-400019, India
,
Lucio Melone*
c  Dipartimento di Chimica, Materiali ed Ingegneria Chimica, ‘G. Natta’, Politecnico Di Milano, via L. Mancinelli, 7, 20131 Milano, Italy   eMail: lucio.melone@polimi.it
,
Atul C. Chaskar*
a  National Centre for Nanosciences and Nanotechnology, University of Mumbai, Vidyanagari, Kalina Campus, Santacruz (East), Mumbai-400098, India   eMail: achaskar25@gmail.com
› Institutsangaben
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Publikationsverlauf

Received: 11. September 2017

Accepted after revision: 12. September 2017

Publikationsdatum:
10. Oktober 2017 (online)


§ Authors contributed equally to this work.

Abstract

A copper-catalyzed expedient, practical, and straightforward approach for the one-pot three-component modular synthesis of multisubstituted imidazoles has been described by using arylacetic acids, N-arylbenzamidines, and nitroalkanes. The reaction involves simultaneous activation of C–H and N–H bonds of arylacetic acids and N-arylbenzamidines, respectively. The use of inexpensive copper sulfate as a catalyst, readily available starting materials, and Celite-free workup makes this protocol economically viable. Multisubstituted imidazoles were obtained in moderate to good yields with significant functional group tolerance and high regioselectivity.

Supporting Information

 
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