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] Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles
Davies, Huw M. L.
Alford, Joshua S.
CHEMICAL SOCIETY REVIEWS, 2014, 43 (15) : 5151 - 5162
[22] Sulfonyl-1,2,3-Triazoles: Convenient Synthones for Heterocyclic Compounds
Zibinsky, Mikhail
Fokin, Valery V.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) : 1507 - 1510
[23] Asymmetric Synthesis of Cyclopropylmethanamines by Rhodium-catalyzed Cyclopropanation of Pinacol Allylboronate with N-Sulfonyl-1,2,3-triazoles
Miura, Tomoya
Nakamuro, Takayuki
Nikishima, Hiroki
Murakami, Masahiro
CHEMISTRY LETTERS, 2016, 45 (08) : 1003 - 1005
[24] Efficient Synthesis of 1-Sulfonyl-1,2,3-triazoles
Raushel, Jessica
Fokin, Valery V.
ORGANIC LETTERS, 2010, 12 (21) : 4952 - 4955
[25] Rh(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-Triazoles with 2,1-Benzisoxazoles or 1,2-Benzisoxazoles
Lei, Xiaoqiang
Gao, Mohan
Tang, Yefeng
ORGANIC LETTERS, 2016, 18 (19) : 4990 - 4993
[26] 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
[27] Synthesis of 2,3-Dihydropyrroles by Rhodium(II)-Catalyzed Transannulation of N-Sulfonyl-1,2,3-triazoles: Diversity Generation by One-Pot Methodologies
Squizatto, Caterina
Bianchini, Maira A.
Delpiccolo, Carina M. L.
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (23) : 16091 - 16103
[28] Rhodium(ii)-catalyzed annulation of N-sulfonyl-1,2,3-triazoles with 1,3,5-triazinanes to produce octahydro-1H-purine derivatives: a combined experimental and computational study
Ge, Jiemin
Wu, Xueli
Bao, Xiaoguang
CHEMICAL COMMUNICATIONS, 2019, 55 (43) : 6090 - 6093
[29] 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
[30] 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

← 1 2 3 4 5 →