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Synthesis 1992; 1992(8): 778-782
DOI: 10.1055/s-1992-26225
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Intermolecular Photoreaction of Thiohomophthalimides with Olefins: Thietane Formation Through [2 + 2] Cycloaddition

Haruko Takechi* , Minoru Machida, Yuichi Kanaoka
  • *Faculty of Pharmaceutical Sciences, Higashi-Nippon-Gakuen University, Ishikari-Tobetu, Hokkaido 061-02, Japan
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Publication Date:
17 September 2002 (online)

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Upon irradiation of thiohomophthalimides (1,2,3,4-tetrahydro-2, 4,4-trimethyl-1,3-dithioxo[3-oxo-l-thioxo or 1-oxo-3-thioxo]iso-quinolines,1-3) in the presence of olefins 4,9, regioselective [2 + 2] cycloaddition occurred to give oxo- or thioxospiro[isoquinoline-1,2′ (or 3,2′)-thietane] derivatives 5, 6, 8, 10-12 and related compounds 1-alkylidene-1,2, 3,4-tetrahydro-2,4,4-trimethyl-3-thioxoisoquinolines 7a, c.