Anion-mediated fragmentation reactions. Mechanistic and synthetic aspects of the fragmentation and rearrangement reactions of pyrimidinedione-alkyne …

VV Kaminski, RN Comber, AJ Wexler…

Index: Kaminski, Victor V.; Comber, Robert N.; Wexler, Allan J.; Swenton, John S. Journal of Organic Chemistry, 1983 , vol. 48, # 14 p. 2337 - 2346

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Citation Number: 7

Abstract

The acetonesensitized photocycloaddition reactions of uracil, thymine, 5-fluorouracil, and & (trimethylsilyl) uracil with alkynes afford 2, 4-diazabicyclo [4.2. 0] oct-7-ene-3, 5-diones. It is noteworthy that 5-(trimethylsily1) uracil gives very high yields in these reactions. High regioselectivity is exhibited for the reaction of uracil, 5-fluorouracil, and & (trimethylsiiyl) uracil with 1-alkynes, the 8-alkyl-substituted product being formed nearly exclusively. ...