One-Pot Synthesis of Benzoxazole/Benzothiazole-Substituted Esters by Michael Addition: A Selective Construction of C-N/C-S Bonds

被引：2

作者：

Gong, Zhi-Ying ^{[1
]}

Yang, Cheng-Li ^{[1
]}

Wang, Dan ^{[1
]}

Huang, Lang ^{[1
]}

Dong, Zhi-Bing ^{[1
,2
,3
]}

机构：

[1] Wuhan Inst Technol, Sch Chem & Environm Engn, Wuhan 430205, Peoples R China

[2] Minist Educ, Wuhan Inst Technol, Key Lab Green Chem Proc, Wuhan 430205, Peoples R China

[3] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Peoples R China

来源：

CATALYSTS | 2023年 / 13卷 / 04期

关键词：

benzoxazole; benzothiazole; synthesis; Michael addition; organosulfur; BIOLOGICAL-ACTIVITIES; BORONIC ACIDS; ARYLATION; BENZOTHIAZOLE; THIOLS; DERIVATIVES;

D O I：

10.3390/catal13040658

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An efficient and convenient synthesis of benzoxazole/benzothiazole-substituted esters in a one-pot strategy is reported. In this investigation, a selective construction of C-N and C-S bonds via simple addition is performed. Thus, using substituted 2-aminophenols/2-aminobenzenethiols, TMTD (tetramethylthiuram disulfide) and alpha,beta-unsaturated esters as starting substrates, C-N and C-S bonds can be selectively constructed by means of the Michael addition reaction. This protocol features high selectivity, high atomic economy, mild conditions, good functional tolerance and good to excellent yields, showing the potential value for the preparation of some biologically and pharmaceutically active compounds.

引用

页数：13

共 45 条

[1] Pd-PVP-Fe (palladium-poly(N-vinylpyrrolidone)-iron) catalyzed S-arylation of thiols with aryl halides in aqueous media
Abadi, Parvaneh Ghaderi-Shekhi
Rafiee, Ezzat
Joshaghani, Mohammad
[J]. INORGANICA CHIMICA ACTA, 2016, 451 : 162 - 170
[2] In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2-thione derivatives
Akhtar, Tashfeen
Hameed, Shahid
Al-Masoudi, Najim A.
Loddo, Roberta
La Colla, Paolo
[J]. ACTA PHARMACEUTICA, 2008, 58 (02) : 135 - 149
[3] AnanEva K.V., 1986, KHIM GETEROTSIKL+, V22, P564, DOI [10.1007/BF00519541, DOI 10.1007/BF00519541]
[4] Azam Mohammed Afzal, 2012, Sci Pharm, V80, P789, DOI 10.3797/scipharm.1204-27
[5] Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: synthesis of diarylsulfides
Bhowmik, Amit
Yadav, Mahesh
Fernandes, Rodney A.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (13) : 2447 - 2458
[6] Development of an Efficient Pd-Catalyzed Coupling Process for Axitinib
Chekal, Brian P.
Guinness, Steven M.
Lillie, Brett M.
McLaughlin, Robert W.
Palmer, Charles W.
Post, Ronald J.
Sieser, Janice E.
Singer, Robert A.
Sluggett, Gregory W.
Vaidyanathan, Rajappa
Withbroe, Gregory J.
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2014, 18 (01) : 266 - 274
[7] Quantitative Structure Activity Relationship (QSAR) Analysis of Substituted 4-Oxothiazolidines and 5-Arylidines as Lipoxygenase Inhibitors
Choudhary, A. N.
Kumar, A.
Juyal, V.
[J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2010, 10 (08) : 705 - 714
[8] Iron-catalyzed S-arylation of thiols with aryl iodides
Correa, Arkaitz
Carril, Monica
Bolm, Carsten
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) : 2880 - 2883
[9] Synthesis of Functionalized Diaryl Sulfides by Cobalt-Catalyzed Coupling between Arylzinc Pivalates and Diaryl Disulfides
Dong, Zhi-Bing
Balkenhohl, Moritz
Tan, Eric
Knochel, Paul
[J]. ORGANIC LETTERS, 2018, 20 (23) : 7581 - 7584
[10] Copper-Catalyzed C(sp2)-S Coupling Reactions for the Synthesis of Aryl Dithiocarbamates with Thiuram Disulfide Reagents
Dong, Zhi-Bing
Liu, Xing
Bolm, Carsten
[J]. ORGANIC LETTERS, 2017, 19 (21) : 5916 - 5919

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