Rh(III)-Catalyzed [4+1] Annulation of Sulfoximines with Maleimides: Access to Benzoisothiazole Spiropyrrolidinediones

被引：7

作者：

Liu, Liansheng ^{[1
]}

Liu, Yiying ^{[1
]}

Li, Shan ^{[1
]}

Gao, Jin ^{[1
]}

Li, Jing ^{[1
]}

Wei, Junfa ^{[1
]}

机构：

[1] Shaanxi Normal Univ, Sch Chem & Chem Engn, Xian 710119, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 06期

基金：

中国国家自然科学基金;

关键词：

C-H BOND; CATALYZED OXIDATIVE ANNULATION; 3-DIMENSIONAL HETEROCYCLES; EFFICIENT SYNTHESIS; METAL-FREE; ACTIVATION; FUNCTIONALIZATION; BENZOTHIAZINES; DERIVATIVES; CYCLIZATION;

D O I：

10.1021/acs.joc.2c02811

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rh(III)-catalyzed synthesis of benzoisothiazole spiropyrrolidinediones using sulfoximine as a directing group under a C-H activation and [4 + 1] annulation strategy with maleimides as a coupling partner is reported. The cyclization reaction was compatible with various substituted sulfoximine and maleimides. The deuterium-labeling studies were performed to investigate the mechanism of the reaction.

引用

页码：3626 / 3635

页数：10

共 85 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine N-Oxides: Approach for the Synthesis of N-Azine Sulfoximines [J].

Aithagani, Sravan Kumar ;

Kumar, Mukesh ;

Yadav, Mahipal ;

Vishwakarma, Ram A. ;

Singh, Parvinder Pal .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (14) :5886-5894

[3]

Allenmark S, 1999, PHOSPHORUS SULFUR, V153, P359

[4] Microbial Transformations of the Taxan Ring of 10-DAB by Some Strains of the Fungus Curvularia lunata: Formation of the Bis-abeotaxanes Wallifoliol and 4-Deacylwallifoliol [J].

Arnone, Alberto ;

Bava, Adriana ;

Fronza, Giovanni ;

Malpezzi, Luciana ;

Nasini, Gianluca .

JOURNAL OF NATURAL PRODUCTS, 2010, 73 (06) :1049-1052

[5] RhIII-Catalyzed C-H Activation: Mizoroki-Heck-Type Reaction of Maleimides [J].

Bettadapur, Kiran R. ;

Sherikar, Mahadev Sharanappa ;

Lanke, Veeranjaneyulu ;

Prabhu, Kandikere Ramaiah .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (07) :1338-1342

[6] Ru (II)-Catalyzed C-H Activation: Ketone-Directed Novel 1,4-Addition of Ortho C-H Bond to Maleimides [J].

Bettadapur, Kiran R. ;

Lanke, Veeranjaneyulu ;

Prabhu, Kandikere Ramaiah .

ORGANIC LETTERS, 2015, 17 (19) :4658-4661

[7] Spectroscopic investigations of bis(sulfoximine) copper(II) complexes and their relevance in asymmetric catalysis [J].

Bolm, C ;

Martin, M ;

Gescheidt, G ;

Palivan, C ;

Neshchadin, D ;

Bertagnolli, H ;

Feth, M ;

Schweiger, A ;

Mitrikas, G ;

Harmer, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6222-6227

[8] An efficient resolution of (+/-)-S-methyl-S-phenylsulfoximine with (+)-10-camphorsulfonic acid by the method of half-quantities [J].

Brandt, J ;

Gais, HJ .

TETRAHEDRON-ASYMMETRY, 1997, 8 (06) :909-912

[9] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].

Chen, Zhengkai ;

Wang, Binjie ;

Zhang, Jitan ;

Yu, Wenlong ;

Liu, Zhanxiang ;

Zhang, Yuhong .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295

[10] 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

← 1 2 3 4 5 6 7 8 9 →