Synthesis of 2-aryl-4H-pyrano[2,3-b]pyridin-4-ones by a one-pot deprotection-cyclization reaction

An efficient synthesis of 2-aryl-4H-pyrano[2,3-b]pyridine-4-ones is reported, using a one-pot, two step process in the presence of pyridinium hydrochloride. The methodology is compatible with a series of functional groups useful for the synthesis of second generation analogs, as part of our SAR prog...

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Published inTetrahedron Vol. 65; no. 34; pp. 6932 - 6940
Main Authors Khlebnikov, Vladimir, Patel, Kalpesh, Zhou, Xiaojian, Reddy, M. Madhava, Su, Zhuoyi, Chiacchia, Fabrizio S., Hansen, Henrik C.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 22.08.2009
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PREVENTION
KETONES
ACID
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Summary:An efficient synthesis of 2-aryl-4H-pyrano[2,3-b]pyridine-4-ones is reported, using a one-pot, two step process in the presence of pyridinium hydrochloride. The methodology is compatible with a series of functional groups useful for the synthesis of second generation analogs, as part of our SAR program. In addition, the method proved to be scalable (>100 g), allowing for efficient synthesis of material to support animal studies. (C) 2009 Elsevier Ltd. All rights reserved.
ISSN:0040-4020
DOI:10.1016/j.tet.2009.06.062