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

共 50 条

[21] Synthesis of Allyl Allenes through Three-Component Cross-Coupling Reaction of N-Tosylhydrazones, Terminal Alkynes, and Allyl Halides
Ye, Fei
Hossain, Mohammad Lokman
Xu, Yan
Ma, Xiaoshen
Xiao, Qing
Zhang, Yan
Wang, Jianbo
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2013, 8 (07) : 1404 - 1407
[22] Copper- and base-free Sonogashira-type cross-coupling reaction of triarylantimony dicarboxylates with terminal alkynes under an aerobic condition
Wang, Xuan
Qin, Weiwei
Kakusawa, Naoki
Yasuike, Shuji
Kurita, Jyoji
[J]. TETRAHEDRON LETTERS, 2009, 50 (46) : 6293 - 6297
[23] Synthesis of graphene nanoribbons through oxidative cross-coupling of arenes with alkynes
Tokoro, Yuichiro
Ohishi, Anna
Fukuzawa, Shin-ichi
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
[24] Palladium-Catalyzed Cross-Coupling Reaction of Bis(cyclopentadienyl)diaryltitaniums with Terminal Alkynes
Murata, Yuki
Nishi, Yuya
Matsumura, Mio
Yasuike, Shuji
[J]. REACTIONS, 2023, 4 (04): : 657 - 666
[25] Synthesis of Aryl Thioethers through the N-Chlorosuccinimide-Promoted Cross-Coupling Reaction of Thiols with Grignard Reagents
Cheng, Jun-Hao
Ramesh, Chintakunta
Kao, Hsin-Lun
Wang, Yu-Jen
Chan, Chien-Ching
Lee, Chin-Fa
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22): : 10369 - 10374
[26] The cross-coupling reaction of vinylindiums generated via hydroindation of terminal alkynes with diaryliodoniums salts
Xue, Z
Yang, DY
Wang, CY
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (1-2) : 247 - 250
[27] A convenient and direct route to phosphinoalkynes via copper-catalyzed cross-coupling of terminal alkynes with chlorophosphanes
Afanasiev, VV
Beletskaya, IP
Kazankova, MA
Efimova, IV
Antipin, MU
[J]. SYNTHESIS-STUTTGART, 2003, Georg Thieme Verlag (18): : 2835 - 2838
[28] Iridium complex-catalyzed cross-coupling reaction of terminal alkynes with internal alkynes via C-H activation of terminal alkynes
Hirabayashi, T
Sakaguchi, S
Ishii, Y
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (06) : 872 - 876
[29] Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential Sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF)
Suzuki, N
Yasaki, S
Yasuhara, A
Sakamoto, T
[J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (10) : 1170 - 1173
[30] Synthesis of nanocatalyst Pd immobilized on ZPD as efficient and reusable for Sonogashira cross-coupling reaction
Najafi, Mehdi
Alinezhad, Heshmatollah
Ghasemi, Shahram
Yeganeh-Salman, Elham
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2022, 980

← 1 2 3 4 5 →