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Synlett 2001; 2001(10): 1523-1526
DOI: 10.1055/s-2001-17447
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Synthesis of Pyridines and Pyrido[2,3-d]pyrimidines by the Lewis Acid Catalysed Bohlmann-Rahtz Heteroannulation Reaction

Mark C. Bagley* , James W. Dale, David D. Hughes, Maren Ohnesorge, Nathan G. Phillips, Justin Bower
  • *Department of Chemistry, Cardiff University, PO Box 912, Cardiff, CF10 3TB, UK; Fax + 44(0)29 20 87 40 30; E-mail: bagleymc@cf.ac.uk
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Publication Date:
27 September 2001 (online)

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Lewis acids catalyse the Bohlmann-Rahtz heteroannulation reaction to generate highly functionalised pyridines from enamino esters and alkynones in a single synthetic step. Of the catalysts studied, ytterbium(III)trifluoromethanesulfonate and zinc(II) bromide are the two most efficient for the synthesis of pyridines and pyrido[2,3-d]pyrimidines, from ethyl β-aminocrotonate or 2,6-diaminopyrimidin-4-one respectively, in up to 94% yield.

pyridines - Bohlmann-Rahtz heteroannulations - heterocycles - Lewis acids