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

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

1
Department of Chemistry, Sciences faculty for Girls, King AbdulAziz University, Jeddah, P.O. Box 13343, Jeddah 21493, Saudi Arabia
2
Department of Chemistry, College of Applied Sciences, Umm Al-Qura University, P.O. Box 13401, Makkah 21955, Saudi Arabia
*
Author to whom correspondence should be addressed.
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 (CC BY 3.0).

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MDPI and ACS Style

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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