Synthesis of pyridines and pyrido[2,3-d]pyrimidines by the Lewis acid catalysed Bohlmann-Rahtz heteroannulation reaction

Authors
Bagley, MC Dale, JW Hughes, DD Ohnesorge, M Phillips, NG Bower, J
Citation
Mc. Bagley et al., Synthesis of pyridines and pyrido[2,3-d]pyrimidines by the Lewis acid catalysed Bohlmann-Rahtz heteroannulation reaction, SYNLETT, (10), 2001, pp. 1523-1526
Citations number
9
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
10
Year of publication
2001
Pages
1523 - 1526
Database
ISI
SICI code
0936-5214(200110):10<1523:SOPAPB>2.0.ZU;2-D
Abstract
Lewis acids catalyse the Bohlmann-Rahtz heteroannulation reaction to genera te highly functionalised pyridines from enamino esters and alkynones in a s ingle synthetic step. Of the catalysts studied, ytterbium(III) trifluoromet hanesulfonate and zinc(II) bromide are the two most efficient for the synth esis of pyridines and pyrido[2,3-d]pyrimidines, from ethyl beta -aminocroto nate or 2,6-diaminopyrimidin-4-one respectively, in up to 94% yield.