One-pot synthesis of iodine-substituted 1,4-oxazepines

Date

2018-02-28

Author

Zora, Metin
KELGÖKMEN, YILMAZ

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A facile one-pot method for the synthesis of iodine-substituted 1,4-oxazepines is reported. When reacted with ZnCl2 and I-2 in DCM at 40 degrees C, N-propargylic beta-enaminones, prepared by the conjugate addition of propargylamine to alpha,beta-alkynic ketones, underwent 7-exo-dig cyclization by zinc chloride and concomitant reaction with molecular iodine to afford 2-(iodomethylene)-2,3-dihydro-1,4-oxazepines in good to high yields. This cyclization was found to occur with broad scope of substrates and high tolerance of functional groups. The resulting iodine-containing 1,4-oxazepines can be further elaborated to more complex structures by subsequent cross-coupling reactions, which may provide a platform for biological studies.

Subject Keywords

Organic Chemistry, Biochemistry, Drug Discovery

URI

https://hdl.handle.net/11511/39526

Journal

TETRAHEDRON LETTERS

DOI

https://doi.org/10.1016/j.tetlet.2018.01.048

Collections

Department of Chemistry, Article

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Citation Formats

M. Zora and Y. KELGÖKMEN, “One-pot synthesis of iodine-substituted 1,4-oxazepines,” TETRAHEDRON LETTERS, pp. 823–827, 2018, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/39526.