Convenient synthesis of 2-alkynylbenzazoles through Sonogashira cross-coupling reaction between thioethers and terminal alkynes

被引：8

作者：

Paun, Anca ^{[1
]}

Matache, Mihaela ^{[1
]}

Enache, Florina ^{[2
]}

Nicolau, Ioana ^{[1
]}

Paraschivescu, Codruta C. ^{[1
]}

Ionita, Petre ^{[1
]}

Zarafu, Irina ^{[1
]}

Parvulescu, Vasile I. ^{[1
]}

Guillaumet, Gerald ^{[2
]}

机构：

[1] Univ Bucharest, Fac Chem, RO-050663 Bucharest, Romania

[2] Univ Orleans, Inst Chim Organ & Analyt, CNRS, UMR 7311, F-45067 Orleans 2, France

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 39期

关键词：

Sonogashira reaction; Benzoxazole; Heteroaromatic thioethers; Cross-coupling reactions; Palladium-catalysis; DIRECT ALKYNYLATION; INHIBITORS; ANALOGS; ACCESS;

D O I：

10.1016/j.tetlet.2015.08.001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe herein the synthesis of 2-alkynylbenzoxazole and 2-alkynylbenzothiazole derivatives through the Sonogashira cross-coupling reaction of the corresponding thioethers and terminal alkynes under aerobic conditions, using Cul and Pd(dppf)Cl-2 as catalysts. The synthetic methodology allows the convenient cross-coupling of heteroaromatic substrates with a wide variety of aromatic and aliphatic alkynes, in moderate to good yields. The behavior of mercapto benzoxazoles and benzothiazoles were also investigated in the desulfitative Sonogashira cross-coupling reaction. It is noteworthy that the reaction occurred better under aerobic conditions rather than an inert atmosphere, although with increased amounts of the diyne side-product. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5349 / 5352

页数：4

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