Flexible application of in synthetic route 6797-13-3

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Evindar, Ghotas; Batey, Robert A. published the article 《Parallel Synthesis of a Library of Benzoxazoles and Benzothiazoles Using Ligand-Accelerated Copper-Catalyzed Cyclizations of ortho-Halobenzanilides》. Keywords: halo benzanilide cyclization benzoaxazole benzothiazole preparation.They researched the compound: 2-Ethylbenzo[d]oxazole( cas:6797-13-3 ).Application of 6797-13-3. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:6797-13-3) here.

A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of o-halobenzanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramol. C-O cross-coupling of the o-halo anilides and is believed to proceed via an oxidative insertion/reductive elimination pathway through a Cu(I)/Cu(III) manifold. The reaction is also applicable to the formation of benzothiazoles. A variety of ligands including 1,10-phenanthroline and N,N’-dimethylethylenediamine ligand acceleration/stabilization in the reaction. Optimal conditions for cyclization used a catalyst combination of CuI and 1,10-phenanthroline (10 mol %). The method was amenable to a parallel-synthesis approach, as demonstrated by the synthesis of a library of benzoxazoles and benzothiazoles substituted at various positions in the ring. Most examples used the cyclization of o-bromo anilides, but o-iodo anilides and o-chloro anilides also undergo a reaction under these conditions. The rate of reaction of the o-halo anilides follows the order I > Br > Cl, consistent with oxidative addition being the rate-determining step.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem