Issue 18, 2010
From the journal:

Organic & Biomolecular Chemistry

Microwave-enhanced synthesis of 2,3,6-trisubstituted pyridazines: application to four-step synthesis of gabazine (SR-95531)†

Navnath Gavande,a   Graham A. R. Johnston,b   Jane R. Hanrahan*a  and  Mary Chebib*a  

* Corresponding authors

a Faculty of Pharmacy. The University of Sydney, Sydney, NSW, Australia
E-mail: janeh@pharm.usyd.edu.au, maryc@pharm.usyd.edu.au
Fax: +61 2 93514391
Tel: +61 2 93518584

b Adrien Albert Laboratory of Medicinal Chemistry, Department of Pharmacology, The University of Sydney, Sydney, NSW, Australia

Abstract

Microwave-enhanced, highly efficient protocols for the synthesis of synthetically and biologically important 2,3,6-trisubstituted pyridazine architectures have been developed by sequential amination/Suzuki coupling/alkylation reactions. This powerful strategy is an economical and highly chemoselective protocol for the synthesis of diversified pyridazines. The total synthesis of gabazine (SR-95531) has been achieved using a versatile strategy in four steps and 73% overall yield.

Graphical abstract: Microwave-enhanced synthesis of 2,3,6-trisubstituted pyridazines: application to four-step synthesis of gabazine (SR-95531)

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Article information

DOI
https://doi.org/10.1039/C0OB00004C
Article type
Paper
Submitted
15 Apr 2010
Accepted
17 Jun 2010
First published
26 Jul 2010

Org. Biomol. Chem., 2010,8, 4131-4136

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Microwave-enhanced synthesis of 2,3,6-trisubstituted pyridazines: application to four-step synthesis of gabazine (SR-95531)

N. Gavande, G. A. R. Johnston, J. R. Hanrahan and M. Chebib, Org. Biomol. Chem., 2010, 8, 4131 DOI: 10.1039/C0OB00004C

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