Microwave-Assisted Cp*CoIII-Catalyzed C-H Activation/Double C-N Bond Formation Reactions to Thiadiazine 1-Oxides

被引：109

作者：

Huang, Jiapian ^{[1
]}

Huang, Yangfei ^{[1
]}

Wang, Tao ^{[1
]}

Huang, Qin ^{[1
]}

Wang, Zhihua ^{[1
]}

Chen, Zhiyuan ^{[1
]}

机构：

[1] Jiangxi Normal Univ, Coll Chem & Chem Engn, Key Lab Funct Small Organ Mol, Minist Educ, 99 Ziyang Rd, Nanchang 330022, Jiangxi, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 05期

基金：

中国国家自然科学基金;

关键词：

ALKYNYLATED SULFOXIMINES; REACTIVITY; DERIVATIVES; AMIDATION; QUINAZOLINES; SULFOXIDES; OXIDATION; ARENES; ACIDS;

D O I：

10.1021/acs.orglett.7b00120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A microwave-assisted, Cp*Co-III-catalyzed direct C-H activation/double C-N bond formation reaction of simple NH-sulfoximines with 1,4,2-dioxazol-5-ones to produce diverse thiadiazine-1-oxides is reported. The reaction tolerates a broad range of functional groups under external oxidant-free conditions and only releases CO2 and H2O as the sole byproducts. The preliminary mechanistic studies revealed an electrophilic

引用

收藏

页码：1128 / 1131

页数：4

相关论文

共 37 条

[1] STEREOSELECTIVE PHARMACOLOGICAL EFFECTS AND BENZODIAZEPINE RECEPTOR AFFINITY OF THE ENANTIOMERS OF GO 4962 [J].

BARTOSZYK, GD ;

DOOLEY, DJ ;

BARTH, H ;

HARTENSTEIN, J ;

SATZINGER, G .

JOURNAL OF PHARMACY AND PHARMACOLOGY, 1987, 39 (05) :407-408

[2] Light-Induced Ruthenium-Catalyzed Nitrene Transfer Reactions: A Photochemical Approach towards N-Acyl Sulfimides and Sulfoximines [J].

Bizet, Vincent ;

Buglioni, Laura ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) :5639-5642

[3] BIOLOGICAL AND BIOCHEMICAL ANTI-HIV ACTIVITY OF THE BENZOTHIADIAZINE CLASS OF NONNUCLEOSIDE REVERSE-TRANSCRIPTASE INHIBITORS [J].

BUCKHEIT, RW ;

FLIAKASBOLTZ, V ;

DECKER, WD ;

ROBERSON, JL ;

PYLE, CA ;

WHITE, EL ;

BOWDEN, BJ ;

MCMAHON, JB ;

BOYD, MR ;

BADER, JP ;

NICKELL, DG ;

BARTH, H ;

ANTONUCCI, TK .

ANTIVIRAL RESEARCH, 1994, 25 (01) :43-56

[4] Dioxazoles, a new mild nitrene transfer reagent in gold catalysis: highly efficient synthesis of functionalized oxazoles [J].

Chen, Ming ;

Sun, Ning ;

Chen, Haoyi ;

Liu, Yuanhong .

CHEMICAL COMMUNICATIONS, 2016, 52 (37) :6324-6327

[5] Copper-Catalyzed N-Alkynylations of Sulfoximines with Bromoacetylenes [J].

Chen, Xiao Yun ;

Wang, Long ;

Frings, Marcus ;

Bolm, Carsten .

ORGANIC LETTERS, 2014, 16 (14) :3796-3799

[6] Transition-Metal-Catalyzed Hydrosulfoximination and Oxidation Reaction for the Synthesis of Sulfoximine Derivatives [J].

Chen, Zhiyuan ;

Huang, Jiapian ;

Wang, Zhijie .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) :9308-9314

[7] Rhodium-Catalyzed ortho-Amidations in the Preparation of Thiadiazine 1-Oxides [J].

Cheng, Ying ;

Dong, Wanrong ;

Wang, Han ;

Bolm, Carsten .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (31) :10821-10824

[8] Regioselective Syntheses of 1,2-Benzothiazines by Rhodium-Catalyzed Annulation Reactions [J].

Cheng, Ying ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (42) :12349-12352

[9] 5,5-dimethyl-1,4,2-dioxazoles as versatile aprotic hydroxamic acid protecting groups [J].

Couturier, M ;

Tucker, JL ;

Proulx, C ;

Boucher, G ;

Dubé, O ;

Andresen, BM ;

Ghosh, A .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4833-4838

[10] SYNTHESIS AND BLOOD-PRESSURE LOWERING ACTIVITY OF 3-(SUBSTITUTED-AMINO)-1,2,4-BENZOTHIADIAZINE 1-OXIDE DERIVATIVES [J].

DILLARD, RD ;

YEN, TT ;

STARK, P ;

PAVEY, DE .

JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (07) :717-722

← 1 2 3 4 →