Sulfur dioxide mediated one-pot, three- and four-component syntheses of polyfunctional sulfonamides and sulfonic esters: Study of the stereoselectivity of the ene reaction of sulfur dioxide

被引：45

作者：

Bouchez, LC ^{[1
]}

Dubbaka, SR ^{[1
]}

Turks, M ^{[1
]}

Vogel, P ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, Inst Chem Sci & Engn, BCH, CH-1015 Lausanne, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 19期

关键词：

D O I：

10.1021/jo049047j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ene reaction of sulfur dioxide with enoxysilanes or with allylsilanes generates silyl sulfinates that can be brominated (Br-2 or NBS) or chlorinated (NCS or Cl-2) to produce the corresponding sulfonyl halides. They react with primary and secondary amines or alcohols to give the corresponding sulfonamides and sulfonic esters, respectively. The hetero-Diels-Alder addition of sulfur dioxide to 1-oxy- or 1,3-dioxy-1,3-dienes generates zwitterions that add to enoxysilanes or allylsilanes giving silyl sulfinates that can be converted in situ into polyfunctional sulfonamides or sulfonic esters. This realizes quick access to libraries of complicated sulfonamides and sulfonic esters applying one-pot, three- and four-component methods.

引用

页码：6413 / 6418

页数：6

共 38 条

[21] Synthesis of pyridopyrimidine derivatives based on benzenesulfonyl acetonitrile compounds via a one-pot sequential four-component domino reaction and microwave-mediated molecular cyclization
Zhang, Zhengyu
Yuan, Ailin
Zheng, Chunling
SYNTHETIC COMMUNICATIONS, 2018, 48 (23) : 2973 - 2982
[22] A mild and highly efficient one-pot three-component reaction for carbon-sulfur bond formation catalyzed by potassium tert-butoxide
Barahman Movassagh
Amir Rakhshani
Chinese Chemical Letters, 2011, 22 (10) : 1179 - 1182
[23] A mild and highly efficient one-pot three-component reaction for carbon-sulfur bond formation catalyzed by potassium tert-butoxide
Movassagh, Barahman
Rakhshani, Amir
CHINESE CHEMICAL LETTERS, 2011, 22 (10) : 1179 - 1182
[24] One-pot synthesis of novel pyrrolo-1,4-benzoxazines via a three- component reaction of 2-amino phenols, acetylenic esters and nitrostyrene derivatives
Loghman Moradi
Mohammad Piltan
Hedieh Rostami
Chinese Chemical Letters, 2014, 25 (01) : 123 - 126
[25] Catalyst-free synthesis of novel 1,5-benzodiazepines and 3,4-dihydroquinoxalines using isocyanide-based one-pot, three- and four-component reactions
Mohlala, Reagan L.
Coyanis, E. Mabel
Fernandes, Manuel A.
Bode, Moira L.
RSC ADVANCES, 2021, 11 (39) : 24466 - 24473
[26] Highly Enantioselective One-Pot, Three-Component Mannich-type Reaction Catalyzed by an N,N′-Dioxide-Scandium(III) Complex
Chen, Shikui
Hou, Zongrui
Zhu, Yin
Wang, Jing
Lin, Lili
Liu, Xiaohua
Feng, Xiaoming
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (24) : 5884 - 5887
[27] TiO2-Mediated, One-Pot, Four-Component 1,3-Dipolar Cycloaddition Reaction: A Facile Synthesis of Dispiro-pyrrolidine Ring Systems
Suresh Babu, A. R.
Raghunathan, R.
SYNTHETIC COMMUNICATIONS, 2009, 39 (02) : 347 - 354
[28] One-Pot, Three-Step Copper-Catalyzed Five-/Four-Component Reaction Constructs Polysubstituted Oxa(Thia)zolidin-2-imines
Madaan, Chetna
Saraf, Shuddham
Priyadarshani, Garima
Reddy, P. Purushotham
Guchhait, Sankar K.
Kunwar, A. C.
Sridhar, B.
SYNLETT, 2012, (13) : 1955 - 1959
[29] Camphorsulfonic Acid-Mediated One-Pot Tandem Consecutive via the Ugi Four-Component Reaction for the Synthesis of Functionalized Indole and 2-Quinolone Derivatives by Switching Solvents
Murugan, Sivan Perumal
Zhong, Hong-Jie
Wu, Chih-Yu
Pan, Hao-Wei
Chen, Chinpiao
Lee, Gene-Hsian
ACS OMEGA, 2022, 7 (07): : 5713 - 5729
[30] Lewis acid-controlled reactions of zirconacyclopentadienes with isocyanates and isothiocyanates. One-pot three- or four-component synthesis of multiply substituted iminocyclopentadienes and butadiene-tethered 1,6-bisamides and electrophilic cyclization
Hu, Qiaoshu
Lu, Jiang
Wang, Congyang
Wang, Chao
Xi, Zhenfeng
TETRAHEDRON, 2007, 63 (28) : 6614 - 6624

← 1 2 3 4 →