Rhodium(II)-Catalyzed Intramolecular Cycloisomerizations of Methylenecyclopropanes with N-Sulfonyl 1,2,3-Triazoles

被引：120

作者：

Chen, Kai ^{[1
,2
]}

Zhu, Zi-Zhong ^{[1
,2
]}

Zhang, Yong-Sheng ^{[3
]}

Tang, Xiang-Ying ^{[3
]}

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

机构：

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

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

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 26期

基金：

中国国家自然科学基金;

关键词：

carbenes; isomerization; nitrogen heterocycles; rhodium; small ring systems; UNIQUE TETRASUBSTITUTED ALKENE; MGI2-MEDIATED RING EXPANSIONS; RH-CATALYZED TRANSANNULATION; TETHERED ALKYLIDENECYCLOPROPANES; CYCLOBUTANE DERIVATIVES; ANALGESIC ACTIVITY; BICYCLIC HOMOLOGS; TERMINAL ALKYNES; BOND-CLEAVAGE; REACTIVITY;

D O I：

10.1002/anie.201402803

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel rhodium(II)-catalyzed tandem cycloisomerization of methylenecyclopropanes (MCPs) with N-sulfonyl 1,2,3-triazoles is disclosed. The reaction produces a series of highly functionalized polycyclic N heterocycles via a rhodium imino carbene intermediate. A distinct feature of this divergent synthesis is that different types of substrates control the reaction pathways. Moreover, several interesting transformations of these products to construct diazabicyclo[3.2.1]octane derivatives are also reported.

引用

页码：6645 / 6649

页数：5

共 50 条

[21] Rhodium Catalyzed Synthesis of Benzopyrans via Transannulation of N-Sulfonyl-1,2,3-triazoles with 2-Hydroxybenzyl Alcohols
Yadagiri, Dongari
Chaitanya, Manthena
Reddy, Angula Chandra Shekar
Anbarasan, Pazhamalai
ORGANIC LETTERS, 2018, 20 (13) : 3762 - 3765
[22] Cycloaddition of N-sulfonyl and N-sulfamoyl azides with alkynes in aqueous media for the selective synthesis of 1,2,3-triazoles
Prasanth, Thumpati
Chakraborti, Gargi
Mandal, Tirtha
Ravichandiran, Velayutham
Dash, Jyotirmayee
GREEN CHEMISTRY, 2022, 24 (02) : 911 - 915
[23] The Divergent Synthesis of Nitrogen Heterocycles by Rhodium(II)-Catalyzed Cycloadditions of 1-Sulfonyl 1,2,3-Triazoles with 1,3-Dienes
Shang, Hai
Wang, Yuanhao
Tian, Yu
Feng, Juan
Tang, Yefeng
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) : 5662 - 5666
[24] Rh(II)-Catalyzed Denitrogenative Reaction of N-Sulfonyl-1,2,3-triazoles with lsatins for the Construction of Indigoids
Pal, Kuntal
Shukla, Rahul K.
Volla, Chandra M. R.
ORGANIC LETTERS, 2017, 19 (21) : 5764 - 5767
[25] Synthesis of N-Acylamidines via Rhodium-Catalyzed Reaction of Nitrosobenzene Derivatives with N-Sulfonyl-1,2,3-triazoles
Ran, Rui-Qiao
Xiu, Shi-Dong
Li, Chuan-Ying
ORGANIC LETTERS, 2014, 16 (24) : 6394 - 6396
[26] Efficient, mild synthesis of N-unsubstituted 1,2,3-triazoles from methanolysis of 1-sulfonyl-1,2,3-triazoles
Rodriguez-Florencio, Janeth
Martinez-Otero, Diego
Garcia-Eleno, Marco A.
Cuevas-Yanez, Erick
SYNTHETIC COMMUNICATIONS, 2018, 48 (17) : 2189 - 2197
[27] Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles to Polysubstituted Pyrroles
Rajasekar, Shanmugam
Anbarasan, Pazhamalai
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17): : 8428 - 8434
[28] Synthesis of Pyrroles from Terminal Alkynes, N-Sulfonyl Azides, and Alkenyl Alkyl Ethers through 1-Sulfonyl-1,2,3-triazoles
Kim, Cheol-Eui
Park, Sangjune
Eom, Dahan
Seo, Boram
Lee, Phil Ho
ORGANIC LETTERS, 2014, 16 (07) : 1900 - 1903
[29] Rh(II)-Catalysed Condensations of N-Sulfonyl-1,2,3-triazoles with Aminals
Saleh, Nidal
Lacour, Jerome
SYNOPEN, 2021, 05 (02): : 134 - 137
[30] 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

← 1 2 3 4 5 →