Copper-Catalyzed Regio- and Stereoselective Oxidative Vinylsulfonylation of Quinoxalinones with Alkynes and Sulfonyl Hydrazides

被引:25
作者
Clinton, Chayan Dhar [1 ]
Prasad, Ch. Durga [1 ]
Thombal, Raju S. [1 ]
Lee, Yong Rok [1 ]
机构
[1] Yeungnam Univ, Sch Chem Engn, Gyongsan 38541, South Korea
基金
新加坡国家研究基金会;
关键词
Quinoxalinones; Vinylsulfonylation; Radical; Alkynes; Peroxide; VINYL SULFONES; QUINOXALIN-2(1H)-ONES; ARYLATION; ALKENES; INHIBITORS; SULFONYLHYDRAZIDES; ESTERIFICATION; ALDEHYDES; ALCOHOLS; DIOXYGEN;
D O I
10.1002/adsc.202001182
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An efficient approach to regio- and stereoselective synthesis of (Z)-vinylsulfonylated quinoxalin-2-ones has been developed. This oxidative reaction involves copper-catalyzed vinylsulfonylation of quinoxalin-2(1H)-ones with alkynes and sulfonyl hydrazides. Various functionalized vinylsulfonylated quinoxalin-2(1H)-one derivatives have been synthesized in excellent yields. The reaction proceeds via sulfonyl radicals generated from sulfonyl hydrazides.
引用
收藏
页码:776 / 784
页数:9
相关论文
共 77 条
[1]   The use of sulfonyl 1,3-dienes in organic synthesis [J].
Backvall, JE ;
Chinchilla, R ;
Najera, C ;
Yus, M .
CHEMICAL REVIEWS, 1998, 98 (06) :2291-2312
[2]   SYNTHESIS OF BETA-AMINO-SULPHONES AND ALPHA-BETA-UNSATURATED SULPHONES [J].
BALASUBRAMANIAN, M ;
BALIAH, V .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (JUN) :1844-1847
[3]   Copper-Catalyzed C(sp2)-C(sp3) Cross-Dehydrogenative Coupling of Quinones with Cyclic Alkanes: One-Step Access to Parvaquone and its Analogs [J].
Baral, Ek Raj ;
Kim, Sung Hong ;
Lee, Yong Rok .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (09) :1134-1141
[4]   Palladium(II)-Catalyzed Oxidative Arylation of Quinoxalin-2(1H)-ones with Arylboronic Acids [J].
Carrer, Amandine ;
Brion, Jean-Daniel ;
Messaoudi, Samir ;
Alami, Mouad .
ORGANIC LETTERS, 2013, 15 (21) :5606-5609
[5]   Reaction of quinoxalin-2-ones with TosMIC reagent:: synthesis of imidazo[1,5-a]quinoxalin-4-ones [J].
Chen, P ;
Barrish, JC ;
Iwanowicz, E ;
Lin, J ;
Bednarz, MS ;
Chen, BC .
TETRAHEDRON LETTERS, 2001, 42 (26) :4293-4295
[6]   Metal-free NaI/TBHP-mediated sulfonylation of thiols with sulfonyl hydrazides [J].
Chen, Qian ;
Huang, Yulin ;
Wang, Xiaofeng ;
Wu, Jiawei ;
Yu, Guodian .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (10) :1713-1719
[7]   THE PREPARATION OF UNSATURATED SULFONES BY CONDENSATION REACTIONS [J].
CHODROFF, S ;
WHITMORE, WF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (03) :1073-1076
[8]  
Das B., 2011, Synthesis, V18, P2941
[9]  
Dumeunier R., 2004, Modern Carbonyl Olefination
[10]   Vinyl Sulfone-Based Peptidomimetics as Anti-Trypanosomal Agents: Design, Synthesis, Biological and Computational Evaluation [J].
Dunny, Elizabeth ;
Doherty, William ;
Evans, Paul ;
Malthouse, J. Paul G. ;
Nolan, Derek ;
Knox, Andrew J. S. .
JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (17) :6638-6650