Synthesis 2016; 48(04): 541-546
DOI: 10.1055/s-0035-1560553
paper
© Georg Thieme Verlag Stuttgart · New York

Iodine-Mediated Synthesis of Novel Pyrazole Derivatives

Mohammad Mahdavi
a   Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran   Email: ashafiee@ams.ac.ir
,
Mahsa Khoshbakht
b   Department of Chemistry, Imam Khomeini International University, Qazvin, Iran
,
Mina Saeedi
c   Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
d   Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
,
Mehdi Asadi
a   Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran   Email: ashafiee@ams.ac.ir
,
Mohammad Bayat
b   Department of Chemistry, Imam Khomeini International University, Qazvin, Iran
,
Alireza Foroumadi
a   Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran   Email: ashafiee@ams.ac.ir
,
Abbas Shafiee*
a   Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran   Email: ashafiee@ams.ac.ir
› Author Affiliations
Further Information

Publication History

Received: 30 September 2015

Accepted after revision: 09 November 2015

Publication Date:
07 January 2016 (online)


Abstract

The reaction between N,2-diarylhydrazinecarbothioamide (generated from arylhydrazines and aryl isothiocyanates) and malononitrile in the presence of iodine/triethylamine in N,N-dimethylform­amide at 80 °C afforded novel pyrazoles, 5-amino-1-aryl-3-(arylamino)-1H-pyrazole-4-carbonitriles, in good yields. In this strategy, iodine served as a versatile desulfurizing agent, efficiently promoting the cyclization reaction.

Supporting Information

 
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