A convenient synthesis of pyridine and 2,2′-bipyridine derivatives

Altuna-Urquijo, Marta, Gehre, Alexander, Stanforth, Stephen and Tarbit, Brian (2009) A convenient synthesis of pyridine and 2,2′-bipyridine derivatives. Tetrahedron, 65 (5). pp. 975-984. ISSN 0040-4020

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Altuna-Urquijo M, Gehre A, Stanforth S, Tarbit B - A convenient synthesis of pyridine... Abstract.pdf

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Official URL: http://dx.doi.org/10.1016/j.tet.2008.11.090

Abstract

α-Chloro-α-acetoxy-β-keto-esters 9 were readily prepared from β-keto-esters 6 in good overall yields. These compounds reacted as α,β-diketo-ester equivalents 2 with amidrazones 1 yielding triazines 3, generally in good yields. Picolinates 10 provided an alternative source of α,β-diketo-ester equivalents 2 when treated with copper(II) acetate. A ‘one-pot’ reaction of the α,β-diketo-ester equivalents 2 with amidrazones 1 in the presence of 2,5-norbornadiene 5 in boiling ethanol yielded the pyridines 4 and 2,2′-bipyridines 4 (R1=2-pyridyl) directly without the need to isolate the corresponding triazines 3. Triazine 3c reacted with the aza-dienophiles 13 and 17 affording the products 16 and 18, respectively, in good yields.

Item Type: Article
Uncontrolled Keywords: pyridines, 2,2′-Bipyridines, 1,2,4-Triazines,Aza Diels–Alder reaction
Subjects: F100 Chemistry
Department: Faculties > Health and Life Sciences > School of Life Sciences > Applied Sciences
Depositing User: EPrint Services
Date Deposited: 25 Feb 2010 10:21
Last Modified: 13 May 2017 06:58
URI: http://nrl.northumbria.ac.uk/id/eprint/2383

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