Synthesis of Bridged N,O-Heterocyclic 1,6-Epoxybenzo[c]azocines via Migration-Annulation Cascade Reaction of α-Imino Rhodium Carbenes

被引：1

作者：

Kong, Xiaoyu ^{[1
]}

Yang, Mingqi ^{[1
]}

Wang, Heng ^{[1
]}

Xu, Ze-Feng ^{[1
]}

Duan, Shengguo ^{[1
]}

Li, Chuan-Ying ^{[1
]}

机构：

[1] Zhejiang Sci Tech Univ, Sch Chem & Chem Engn, Key Lab Surface & Interface Sci Polymer Mat Zhejia, Hangzhou 310018, Peoples R China

来源：

CHEMISTRYSELECT | 2023年 / 8卷 / 26期

基金：

中国国家自然科学基金;

关键词：

carbenes; heterocycle; rearrangement; triazoles; zwitterions; C-H BOND; STEREOSELECTIVE-SYNTHESIS; CYCLIZATION; ZWITTERIONS; ALKALOIDS; ACCESS; ARYL;

D O I：

10.1002/slct.202301685

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A rhodium-catalyzed cascade migration-annulation reaction of 1-sulfonyl-1,2,3-triazole has been developed. As the key step, the 1,3-sulfinate migration of & alpha;-imino rhodium carbene yielded an extended zwitterion, which was intramolecularly trapped by aldehyde group furnishing bridged N,O-heterocyclic 1,6-epoxybenzo[c]azocine as the [5+2] cyclization product. This migration-annulation strategy provides more flexibility for heterocycle synthesis and medium-sized ring construction, especially for the construction of polycycles with complex skeletons.

引用

页数：4

共 3 条

[1] Synthesis of Cyclopenta[b]indoles via Rhodium-Catalyzed Cascade Migration-Annulation of 1-Sulfonyl-1,2,3-triazoles and Indoles
Xu, Huaping
Wang, Heng
Xu, Ze-Feng
Duan, Shengguo
Li, Chuan-Ying
ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (10) : 1623 - 1628
[2] Rh(III)-Catalyzed Cascade Annulation/C-H Attivation of o-Ethynylanilines with Diazo Compounds: One-Pot Synthesis of Benzo[a]carbazoles via 1,4-Rhodium Migration
Guo, Songjin
Yuan, Kai
Gu, Meng
Lin, Aijun
Yao, Hequan
ORGANIC LETTERS, 2016, 18 (20) : 5236 - 5239
[3] Rhodium-Catalyzed Cascade Annulation Reaction via C-H Activation of Azobenzenes with Terminal Alkynes: A Synthesis of Indolo[1,2-b]cinnolines
Zhang, Shuwei
Wang, Biying
Jia, Xiaodong
Yuan, Yu
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (03) : 451 - 455

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