Accidental discovery of a 'longer-range' vinylogous Pummerer-type lactonization: formation of sulindac sulfide lactone from sulindac

作者：Halder Somnath; Satyam Apparao^*

来源：Tetrahedron Letters, 2011, 52(11): 1179-1182.

DOI：10.1016/j.tetlet.2011.01.008

• Sulindac sulfide
• Sulindac sulfide lactone
• Longer-range vinylogous Pummerer-type
• lactonization

Unexpected formation of sulindac sulfide lactone occurred when sulindac was treated with oxalyl chloride and triethylamine. Structurally analogous sulindac sulfide and indomethacin did not undergo such lactonization under similar reaction conditions. We believe that the sulfoxide function in sulindac plays a pivotal role possibly via a 'longer-range' vinylogous Pummerer-type reaction as a driving force for the observed lactonization. The structure of the lactone was confirmed by single crystal X-ray analysis.

• 出版日期2011-3-16