Synthesis 2012; 44(23): 3649-3654
DOI: 10.1055/s-0032-1317515
paper
© Georg Thieme Verlag Stuttgart · New York

One-Pot, Four-Component Synthesis of Novel Imidazo[2,1-b]thiazol-5-amine Derivatives

Mohammad Mahdavi
a   Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran
,
Mehdi Asadi
b   School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran   Fax: +98(21)66461178   Email: ashafiee@ams.ac.ir
,
Mina Saeedi
a   Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran
,
Mostafa Ebrahimi
a   Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran
,
Mohammad A. Rasouli
b   School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran   Fax: +98(21)66461178   Email: ashafiee@ams.ac.ir
,
Parviz R. Ranjbar
b   School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran   Fax: +98(21)66461178   Email: ashafiee@ams.ac.ir
,
Alireza Foroumadi
a   Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran
,
Abbas Shafiee*
a   Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran
› Author Affiliations
Further Information

Publication History

Received: 31 July 2012

Accepted after revision: 10 October 2012

Publication Date:
12 November 2012 (online)


Abstract

Novel imidazo[2,1-b]thiazol-5-amine derivatives were synthesized by a one-pot, four-component reaction of 2-bromoacetophenone derivatives, aromatic aldehydes, thiourea, and isocyanides in the presence of ammonium chloride (NH4Cl) in toluene under reflux conditions. Moderate to good yields resulted and the reaction showed tolerance toward a range of aromatic aldehydes with electron-donating and electron-withdrawing substituents on either­ para or ortho positions.