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

Research output: Contribution to journalArticle

53 Citations (Scopus)

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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Cyclization
Alkylation
chloroacetamide
acetonitrile
3-hydroxypyridine
cesium carbonate

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., ... 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

A one-pot synthesis of pyrido[2,3.b][1,4]oxazin-2-ones. / Cho, Su Dong; Park, Yong Dae; Kim, Jeum Jong; Lee, Sang Gyeong; Ma, Chen; Song, Sang Yong; Joo, Woo Hong; Falck, J R; Shiro, Motoo; Shin, Dong Soo; Yoon, Yong Jin.

In: Journal of Organic Chemistry, Vol. 68, No. 20, 03.10.2003, p. 7918-7920.

Research output: Contribution to journalArticle

Cho, SD, Park, YD, Kim, JJ, Lee, SG, Ma, C, Song, SY, Joo, WH, Falck, JR, Shiro, M, Shin, DS & Yoon, YJ 2003, 'A one-pot synthesis of pyrido[2,3.b][1,4]oxazin-2-ones', Journal of Organic Chemistry, vol. 68, no. 20, pp. 7918-7920. https://doi.org/10.1021/jo034593i
Cho SD, Park YD, Kim JJ, Lee SG, Ma C, Song SY et al. A one-pot synthesis of pyrido[2,3.b][1,4]oxazin-2-ones. Journal of Organic Chemistry. 2003 Oct 3;68(20):7918-7920. https://doi.org/10.1021/jo034593i
Cho, Su Dong ; Park, Yong Dae ; Kim, Jeum Jong ; Lee, Sang Gyeong ; Ma, Chen ; Song, Sang Yong ; Joo, Woo Hong ; Falck, J R ; Shiro, Motoo ; Shin, Dong Soo ; Yoon, Yong Jin. / A one-pot synthesis of pyrido[2,3.b][1,4]oxazin-2-ones. In: Journal of Organic Chemistry. 2003 ; Vol. 68, No. 20. pp. 7918-7920.
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AU - Joo, Woo Hong

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AU - Yoon, Yong Jin

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