Synlett 2016; 27(20): 2795-2798
DOI: 10.1055/s-0036-1588595
letter
© Georg Thieme Verlag Stuttgart · New York

Zinc Chloride Catalyzed, Dipolar Aprotic Solvent-Mediated, One-Pot Synthesis of 2-[(Benzo[d]thiazol-2-ylamino)(phenyl)methyl]phenols

Vandana Cherkadu
a   Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India   Email: priyabs_chem@yahoo.com
b   R&D Centre, CJEX Biochem, 7&8, 2nd cross, Muniswamappa layout, Hosur Road, Bommanahalli, Bangalore 560 068, India
,
Praveen Kumar Kalavagunta
c   Crop Protection Chemicals Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad, 500 007, India
,
Narender Ravirala
c   Crop Protection Chemicals Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad, 500 007, India
,
Nanjunda Swamy Shivananju
d   Department of Biotechnology, Sri Jayachamarajendra College of Engineering, Mysore-570006, India
,
Babu Shubha Priya*
a   Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India   Email: priyabs_chem@yahoo.com
› Author Affiliations
Further Information

Publication History

Received: 05 July 2016

Accepted after revision: 27 August 2016

Publication Date:
08 September 2016 (online)


Both the authors contributed equally.

Abstract

A three-component one-pot method has been developed for the synthesis of 2-[(benzo[d]thiazol-2-ylamino)(phenyl)methyl]phenols from a variety of aldehydes, 2-amino-1,3-benzothiazoles, and phenols. Phenol, substituted phenols, and polyhydroxybenzenes participated well, providing the corresponding derivatives in good yields. In the case of polyhydroxybenzenes, for which the formation of positional isomers or dimers might have been possible, the sterically less hindered positional isomer was formed exclusively via the ortho-quinone methide.

Supporting Information

 
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