Y Zinc Chloride Mediated Synthesis of 1,4-Oxazepines from N-Propargylic -Enaminones

Date

2017-12-22

Author

Kelgokmen, Yılmaz
Çayan, Yasemin
Zora, Metin

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An efficient and general method for the synthesis of 1,4-oxazepines is described. When reacted with ZnCl2 in DCM at 40 degrees C or CHCl3 at 61 degrees C, N-propargylic -enaminones undergo 7-exo-dig cyclization to afford 2-methylene-2,3-dihydro-1,4-oxazepines in good to high yields. This cyclization has been found to be general for a diverse range of N-propargylic -enaminones, and proceeds with high efficiency and with broad functional group tolerance. The reactions in refluxing CHCl3 produced 1,4-oxazepines in comparatively short reaction times and with better yields that those obtained in refluxing DCM. This operationally easy method may provide rapid access to a library of functionalized 1,4-oxazepine derivatives of pharmacological interest.

Subject Keywords

Heterocycles, Cyclization, Alkynes, Lewis acids, Synthetic methods

URI

https://hdl.handle.net/11511/37981

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

DOI

https://doi.org/10.1002/ejoc.201701433

Collections

Department of Chemistry, Article

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Citation Formats

Y. Kelgokmen, Y. Çayan, and M. Zora, “Y Zinc Chloride Mediated Synthesis of 1,4-Oxazepines from N-Propargylic -Enaminones,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, pp. 7167–7178, 2017, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/37981.