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Molecules 2013, 18(1), 535-544; doi:10.3390/molecules18010535
Article

Enaminonitriles in Heterocyclic Synthesis: A Route to 1,3-Diaryl-4-aminopyrazole Derivatives

1, 1,*  and 2
Received: 29 October 2012 / Revised: 15 November 2012 / Accepted: 24 December 2012 / Published: 2 January 2013
(This article belongs to the Section Organic Synthesis)
Download PDF [195 KB, 18 June 2014; original version 18 June 2014]

Abstract

Benzylcyanide and 4-nitrobenzylcyanide condensed with triethyl orthoformate and piperidine or morpholine to yield 2-aryl-2-piperidinyl or 2-morpholinylacrylonitriles. These coupled with aromatic diazonium salts to yield the 2-arylhydrazno-2-arylethane nitriles in good yields. The latter were converted into 4-aminopyrazoles in good yields using the Thorpe-Ziegler cyclization.
Keywords: enaminonitriles; 4-aminopyrazole; Thorpe-Ziegler cyclization; microwave irradiation enaminonitriles; 4-aminopyrazole; Thorpe-Ziegler cyclization; microwave irradiation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Medrasi, H.Y.; Al-Sheikh, M.A.; Salaheldin, A.M. Enaminonitriles in Heterocyclic Synthesis: A Route to 1,3-Diaryl-4-aminopyrazole Derivatives. Molecules 2013, 18, 535-544.

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