Transformation of Alkyl N-(Vinyloxy)benzimidates to Alkyloxazoles. Mechanism and Extension

DOI: 10.1246/bcsj.67.2219

Source and publish data:

Bulletin of the Chemical Society of Japan p. 2219 - 2226 (1994)

Update date:2022-07-30

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Authors:

Yokoyama, Masataka

Menjo, Yasuhiro

Ubukata, Makoto

Irie, Masakazu

Watanabe, Mikari

Togo, Hideo

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Article abstract of DOI:10.1246/bcsj.67.2219

Transformation of alkyl N-(vinyloxy)benzimidates to alkyloxazoles proceeds through the intermediates: a charge-separated 1,2-oxazetidine derivative and then 1-hydroxy-2-<imino>maleic acid diester, while their photochemical transformation takes place via a concerted <1.3> sigmatropic shift.As the extension of this reaction, the preparation of the precursor proposed for virginiamycin M2 synthesis and the reaction of N-analogs of alkyl N-(vinyloxy)benzimidates are described.

Full text of DOI:10.1246/bcsj.67.2219

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