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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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

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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