Synthesis of 2-Alkylidene-3,1-Benzoxathiin-4-Ones by the Pummerer Type Reaction

Masaki YamanakaDepertment of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda,, Chiba278-8510, Japan

Shigeru ShimadaNational Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki305-8565, Japan

Wataru AndoNational Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki305-8565, Japan

Takeo KonakaharaDepertment of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda,, Chiba278-8510, Japan

Norio SakaiDepertment of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda,, Chiba278-8510, Japan

Masao ShimizuNational Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki305-8565, JapanCorrespondence[email protected]

GRAPHICAL ABSTRACT

Abstract

We investigated synthesis of 2-alkylidene-3,1-benzoxathiin-4-ones (2-alkylidene BOTs) from 2-alkyl BOTs with the Pummerer type reaction. The reaction of 2-alkyl BOT 1-oxides, which were obtained by oxidation of 2-alkyl BOTs with mCPBA, with trifluoroacetic anhydride was carried out in the presence of pyridine at 100 °C for 3 h. Consequently, 2-alkylidene BOTs were obtained in 30–88% yields.

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Synthesis of 2-Alkylidene-3,1-Benzoxathiin-4-Ones by the Pummerer Type Reaction

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Synthesis of 2-Alkylidene-3,1-Benzoxathiin-4-Ones by the Pummerer Type Reaction

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