Rhodium(II)-Catalyzed and Thermally Induced Intramolecular Migration of N-Sulfonyl-1,2,3-triazoles: New Approaches to 1,2-Dihydroisoquinolines and 1-Indanones

被引：39

作者：

Sun, Run ^{[1
,2
]}

Jiang, Yu ^{[1
,2
]}

Tang, Xiang-Ying ^{[3
]}

Shi, Min ^{[1
,2
,3
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Meilong Rd 130, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Meilong Rd 130, Shanghai 200237, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 16期

基金：

中国国家自然科学基金;

关键词：

carbenes; heterocycles; rearrangement; rhodium; triazoles; ONE-POT SYNTHESIS; TANDEM NUCLEOPHILIC-ADDITION; N-SULFONYL 1,2,3-TRIAZOLES; FRIEDEL-CRAFTS REACTION; TERMINAL ALKYNES; AZAVINYL CARBENES; STEREOCONTROLLED SYNTHESIS; 3-COMPONENT REACTION; EFFICIENT SYNTHESIS; FACILE SYNTHESIS;

D O I：

10.1002/chem.201504914

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

New rhodium(II)-catalyzed or thermally induced intramolecular alkoxy group migration of N-sulfonyl-1,2,3-triazoles has been developed, affording divergent synthesis of 1,2-dihydroisoquinoline and 1-indanone derivatives according to different conditions. N-Sulfonyl keteneimine is the key intermediate for the synthesis of dihydroisoquinoline, whereas the aza-vinyl carbene intermediate results in the formation of 1-indanone.

引用

页码：5727 / 5733

页数：7

共 50 条

[21] Rhodium(II)-catalyzed intramolecular annulation of 1-sulfonyl-1,2,3-triazoles with indoles: facile synthesis of functionalized tetrahydro-β-carbolines
Shang, Hai
Tian, Yu
Luo, Jun
Li, Lingyu
Tang, Yefeng
Zou, Zhongmei
RSC ADVANCES, 2016, 6 (37): : 30835 - 30839
[22] Rhodium(II)-Catalyzed Intramolecular Annulation of 1-Sulfonyl-1,2,3Triazoles with Pyrrole and Indole Rings: Facile Synthesis of N-Bridgehead Azepine Skeletons
Yang, Jin-Ming
Zhu, Cheng-Zhi
Tang, Xiang-Ying
Shi, Min
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (20) : 5142 - 5146
[23] Rhodium-catalyzed synthesis of multi-substituted furans from N-sulfonyl-1,2,3-triazoles bearing a tethered carbonyl group
Zhang, Wen-Biao
Xiu, Shi-Dong
Li, Chuan-Ying
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (01): : 47 - 50
[24] Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles
Miura, Tomoya
Biyajima, Tsuneaki
Fujii, Tetsuji
Murakami, Masahiro
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) : 194 - 196
[25] Rhodium-Catalyzed Tandem Cyclopropanation/Cope Rearrangement of 4-Alkenyl-1-sulfonyl-1,2,3-triazoles with Dienes
Parr, Brendan T.
Davies, Huw M. L.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) : 10044 - 10047
[26] Direct Production of Enaminones from Terminal Alkynes via Rhodium-Catalyzed Reaction of Formamides with N-Sulfonyl-1,2,3-triazoles
Miura, Tomoya
Funakoshi, Yuuta
Tanaka, Takamasa
Murakami, Masahiro
ORGANIC LETTERS, 2014, 16 (10) : 2760 - 2763
[27] Synthesis of α,β,γ,δ-Unsaturated Imines from N-Sulfonyl-1,2,3-triazoles and Allenes through Rhodium-catalyzed Cyclopropanation and Thermal Rearrangement
Miura, Tomoya
Nakamuro, Takayuki
Biyajima, Tsuneaki
Murakami, Masahiro
CHEMISTRY LETTERS, 2015, 44 (05) : 700 - 702
[28] Synthesis of Penta-2,4-dien-1-imines and 1,2-Dihydropyridines by Rhodium-Catalyzed Reaction of N-Sulfonyl-1,2,3-triazoles with 2-(Siloxy)furans
Funakoshi, Yuuta
Miura, Tomoya
Murakami, Masahiro
ORGANIC LETTERS, 2016, 18 (24) : 6284 - 6287
[29] Rhodium(II)-Catalyzed Formal [3+2] Cycloaddition of N-Sulfonyl-1,2,3-triazoles with Isoxazoles: Entry to Polysubstituted 3-Aminopyrroles
Lei, Xiaoqiang
Li, Longbo
He, Yu-Peng
Tang, Yefeng
ORGANIC LETTERS, 2015, 17 (21) : 5224 - 5227
[30] Rh(II)/Mg(OtBu)2-Catalyzed Tandem One-Pot Synthesis of 1,4-Oxazepines and 1,4-Oxazines from N-Sulfonyl-1,2,3-triazoles and Glycidols
Ko, Young Ok
Jeon, Hyun Ji
Jung, Da Jung
Kim, U. Bin
Lee, Sang-gi
ORGANIC LETTERS, 2016, 18 (24) : 6432 - 6435

← 1 2 3 4 5 →