Novel synthesis of pyridazino[4,5-b][1,4]oxazin-3,8-diones

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

Research output: Contribution to journalArticle

23 Scopus citations

Abstract

A novel and effective synthesis of pyridazino[4,5-b][1,4]oxazin-3,8-diones via Smiles rearrangement is presented. Treatment of N-substituted 2-chloro(or hydroxy)acetamide, 2-tetrahydropyranyl-4-chloro-5-hydroxy(or chloro)pyridazin-3-one and cesium carbonate in refluxing acetonitrile was afforded the corresponding pyridazino[4,5-b][1,4]oxazin-3,8-diones in excellent yield.

Original languageEnglish (US)
Pages (from-to)8995-8998
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number50
DOIs
StatePublished - Dec 8 2003

Keywords

  • Pyrodazino[4,5-b][1,4]oxazine
  • Smiles rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Cho, S. D., Song, S. Y., Park, Y. D., Kim, J. J., Joo, W. H., Shiro, M., Falck, J. R., Shin, D. S., & Yoon, Y. J. (2003). Novel synthesis of pyridazino[4,5-b][1,4]oxazin-3,8-diones. Tetrahedron Letters, 44(50), 8995-8998. https://doi.org/10.1016/j.tetlet.2003.09.216