Divergent, generalized synthesis of unsymmetrically substituted 2, 5-piperazinediones

…, RW Armstrong, LK Maruyama, JS Dung…

Index: Williams, Robert M.; Armstrong, Robert W.; Maruyama, Lynn K.; Dung, Jen-Sen; Anderson, Oren P. Journal of the American Chemical Society, 1985 , vol. 107, # 11 p. 3246 - 3253

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Citation Number: 34

Abstract

Abstract: N, N'-Disubstituted 2, 5-piperazinediones (12) can be 3, 6-dibrominated followed by displacement with sodium 2-mercaptopyridine to furnish syn-l, 4disubstituted 3, 6-bis (2'- thiopyridyl)-2, 5-piperazinediones (8) in high yield. Precomplexation of these sulfides with silver (1) triflate followed by addition of trimethylsilyl enol ethers leads to chemoselective CC bond formation, furnishing the homologated piperazinediones 10. The remaining sulfide ...