Synthesis of. alpha.,. beta.-epoxyacyl azides and their rearrangement to epoxy isocyanates and 3-and 4-oxazolin-2-ones

JM Lemmens, WWJM Blommerde, L Thijs…

文献索引：Lemmens, Jacques M.; Blommerde, Willem W. J. M.; Thijs, Lambertus; Zwanenburg, Binne Journal of Organic Chemistry, 1984 , vol. 49, # 12 p. 2231 - 2235

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被引用次数: 19

摘要

The conversion of cu, Bepoxy carboxylates 6 into cu, p-epoxyacyl azides 4 proceeds either via reaction of the mixed anhydrides 7 with sodium azide or via reaction of epoxyacyl chlorides 8 with hydrazoic acid-pyridine. The latter method is preferred. The azides 4 undergo a smooth thermal Curtius rearrangement to give 4-oxazolin-2-ones 10 for the substrates 4a-h having a hydrogen atom at C,. Monitoring this reaction by means of IR ...