Rhodium-catalyzed benzoisothiazole synthesis by tandem annulation reactions of sulfoximines and activated olefins

被引：24

作者：

Li, Yang ^{[1
]}

Dong, Lin ^{[1
]}

机构：

[1] Sichuan Univ, West China Sch Pharm, Educ Minist, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu 610041, Sichuan, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 47期

关键词：

C-BOND FORMATION; NH-SULFOXIMINES; OXIDATIVE OLEFINATION; BENZOIC-ACIDS; RING-SYSTEMS; ONE-POT; ALKYNES; 1,2-BENZOTHIAZINES; FUNCTIONALIZATION; STRATEGIES;

D O I：

10.1039/c7ob02586f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(III)-catalyzed N-directed ortho C-H activation reactions have been developed for the synthesis of unique heterocyclic benzoisothiazoles. Herein, this novel tandem annulation approach can efficiently construct benzoisothiazole compounds from free NH-sulfoximines and alkenes via C-H activation, olefination and subsequent intramolecular aza-Michael cyclization.

引用

页码：9983 / 9986

页数：4

共 50 条

[21] Rhodium-Catalyzed Synthesis and Reactions of N-Acylphthalimides
Li, Guangzhe
Arisawa, Mieko
Yamaguchi, Masahiko
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2 (11) : 983 - 988
[22] Rhodium-Catalyzed Allylation Reactions
Thoke, Mahesh Bhagwan
Kang, Qiang
SYNTHESIS-STUTTGART, 2019, 51 (13): : 2585 - 2631
[23] Synthesis and functionalization of indoles through rhodium-catalyzed reactions
Patil, Shivaputra
Patil, Renukadevi
CURRENT ORGANIC SYNTHESIS, 2007, 4 (02) : 201 - 222
[24] RHODIUM-CATALYZED SYNTHESIS OF TRISUBSTITUTED OLEFINS FROM ETHENE DERIVATIVES AND DIAZOALKANES
WOLF, J
BRANDT, L
FRIES, A
WERNER, H
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (05): : 510 - 512
[25] THE RHODIUM-CATALYZED HYDROBORATION OF OLEFINS - A MECHANISTIC INVESTIGATION
EVANS, DA
FU, GC
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08): : 2280 - 2282
[26] Rhodium-catalyzed silylative coupling of olefins with vinylsilanes
Marciniec, B
Walczuk-Gusciora, E
Pietraszuk, C
CATALYSIS LETTERS, 1998, 55 (02) : 125 - 127
[27] Annulation of alkenyl-substituted heterocycles via rhodium-catalyzed intramolecular C-H activated coupling reactions
Tan, KL
Bergman, RG
Ellman, JA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (11) : 2685 - 2686
[28] Rhodium-Catalyzed Amination of Aromatic Olefins [1]
Annegret Tillack
Harald Trauthwein
Christian G. Hartung
Martin Eichberger
Stephan Pitter
Achim Jansen
Matthias Beller
Monatshefte für Chemie / Chemical Monthly, 2000, 131 : 1327 - 1334
[29] Rhodium-Catalyzed Hydrocarboxylation of Olefins with Carbon Dioxide
Kawashima, Shingo
Aikawa, Kohsuke
Mikami, Koichi
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (19) : 3166 - 3170
[30] Rhodium-catalyzed tandem aldol condensation-Robinson annulation between aldehydes and acetone: synthesis of 3-methylcyclohexenones
Wang, Fen
Liu, Yuchen
Qi, Zisong
Dai, Wei
Li, Xingwei
TETRAHEDRON LETTERS, 2014, 55 (47) : 6399 - 6402

← 1 2 3 4 5 →