Tetrahedron

Ring closure reactions of β-nitroso-, β-acyl-, and β-thiocarbamoyl-α, β-unsaturated sulfilimines. Synthesis of [1, 2, 5] oxadiazolo [3, 4-d]-, isoxazolo [3, 4-d]-, and …

N Matsumoto, M Takahashi

Index: Matsumoto, Nobuaki; Takahashi, Masahiko Tetrahedron, 2002 , vol. 58, # 50 p. 10073 - 10079

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Citation Number: 11

Abstract

1, 3-Dialkyl-6-chlorouracils were treated with S, S-diphenylsulfilimine to give N-(1, 3- dialkyluracil-6-yl)-S, S-diphenylsulfilimines. The uracilylsulfilimines were nitrosated, acylated, or thiocarbamoylated to give N-(5-nitroso-, 5-acyl-, or 5-thiocarbamoyluracil-6-yl) sulfilimines, respectively. These conjugated sulfilimines were cyclized by thermolysis or photolysis to [1, 2, 5] oxadiazolo [3, 4-d], isoxazolo [3, 4-d], or isothiazolo [3, 4-d] ...