A one-pot synthesis of pyrido[2,3.b][1,4]oxazin-2-ones

Su Dong Cho, Yong Dae Park, Jeum Jong Kim, Sang Gyeong Lee, Chen Ma, Sang Yong Song, Woo Hong Joo, J R Falck, Motoo Shiro, Dong Soo Shin, Yong Jin Yoon

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53 Scopus citations

Abstract

Pyrido[2,3-b][1,4]oxazin-2-ones are conveniently prepared in excellent yields by a one-pot annulation of N-substituted-2-chloroacetamides with 2-halo-3-hydroxypyridines with use of cesium carbonate in refluxing acetonitrile. The key transformation features a Smiles rearrangement of the initial O-alkylation product and subsequent cyclization.

Original languageEnglish (US)
Pages (from-to)7918-7920
Number of pages3
JournalJournal of Organic Chemistry
Volume68
Issue number20
DOIs
StatePublished - Oct 3 2003

ASJC Scopus subject areas

  • Organic Chemistry

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    Cho, S. D., Park, Y. D., Kim, J. J., Lee, S. G., Ma, C., Song, S. Y., Joo, W. H., Falck, J. R., Shiro, M., Shin, D. S., & Yoon, Y. J. (2003). A one-pot synthesis of pyrido[2,3.b][1,4]oxazin-2-ones. Journal of Organic Chemistry, 68(20), 7918-7920. https://doi.org/10.1021/jo034593i