Journal
TETRAHEDRON
Volume 66, Issue 25, Pages 4542-4550Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.04.059
Keywords
Salicylaldehyde; Pyridinium chloride; Chromene; Imidazo[1,2-a]pyridine; Cascade reaction
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Funding
- Fundacao para a Ciencia e a Tecnologia [PPCDT/QUI/59356/2004]
- [SFRH/BD/31531/2006]
- Fundação para a Ciência e a Tecnologia [SFRH/BD/31531/2006] Funding Source: FCT
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The chromeno-imidazo[1,2-a]pyridine scaffold was generated in an one pot condensation/cyclization reaction involving a salicylaldehyde and 1-(cyanomethyl)pyridinium chloride, in aqueous sodium carbonate solution. These novel compounds were isolated in 47-71% yield. The reaction pathway was followed by H-1 NMR spectroscopy allowing a clear understanding of the side reactions involved in the process. Different mono-substituted pyridinium chlorides were synthesized and reacted with mono-substituted salicylaldehydes and a detailed discussion of the scope of the synthetic method is also presented. (C) 2010 Elsevier Ltd. All rights reserved.
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