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

Mohammad Mahdavi; Mehdi Asadi; Mina Saeedi; Mostafa Ebrahimi; Mohammad A. Rasouli; Parviz R. Ranjbar; Alireza Foroumadi; Abbas Shafiee

doi:10.1055/s-0032-1317515

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(23): 3649-3654
DOI: 10.1055/s-0032-1317515

paper

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

Mohammad Mahdavi

^aDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran

,

Mehdi Asadi

^bSchool 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

^aDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran

,

Mostafa Ebrahimi

^aDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran

,

Mohammad A. Rasouli

^bSchool 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

^bSchool 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

^aDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran

,

Abbas Shafiee*

^aDepartment of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran 14176, Iran

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Abstract

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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.

Key words

heterocyclic compounds - multicomponent reactions - isocyanides - thiourea - ammonium chloride

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Referenzen

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