Abstract
Reaction of 4-substituted benzoic acid derivatives with (N-isocyanimino)-triphenylphosphorane proceeds smoothly at room temperature to afford the corresponding 2-aryl-1,3,4-oxadiazoles via an intramolecular aza-Wittig reaction in excellent yields under neutral conditions. The structures of the products were deduced from their IR, 1 H NMR, and 13 C NMR spectra, and mass spectrometry.
Highlights
Isocyanide-based reactions have been known for about 80 years, with the first described in 1921 and named after its founder, Passerini.[1,2]
The classical syntheses of isocyanides were developed in 1867 by Gautier.[4]
For a whole century, from 1859 to 1958, isocyanides were not readily available, and the chemistry of the isocyanides remained an under-investigated part of organic chemistry.[5]
Summary
Isocyanide-based reactions have been known for about 80 years, with the first described in 1921 and named after its founder, Passerini.[1,2] The chemistry of the isocyanides began in 1859 when Lieke prepared allyl isocyanide as the first isocyanide.[3]. The intramolecular version of the aza-Wittig-type reaction has attracted considerable attention recently because of its high potential for the synthesis of a wide variety of nitrogen heterocycles, which can be attributed, in good measure, to the rapid progress in the preparation of functionalized iminophosphoranes.
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