Synthesis of Spiro 3,3′-Cyclopropyl Oxindoles Via N-Bromosuccinimide-Mediated Ring-Closing and Contraction Cascade

被引：8

作者：

Zhang, Rui-Ying ^{[1
,2
]}

Jin, Feng ^{[1
,2
]}

Bao, Xiao-Guang ^{[1
,2
]}

Li, Hai-Yan ^{[3
]}

Xu, Xiao-Ping ^{[1
,2
]}

Ji, Shun-Jun ^{[1
,2
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

[2] Soochow Univ, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Suzhou 215123, Peoples R China

[3] Soochow Univ, Anal & Testing Ctr, Suzhou 215123, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 01期

基金：

中国国家自然科学基金;

关键词：

REVERSE-TRANSCRIPTASE INHIBITORS; BIOLOGICAL EVALUATIONS; CYCLOPROPANATION; DESIGN; DISCOVERY; INDOLES;

D O I：

10.1021/acs.joc.0c02610

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An N-bromosuccinimide-mediated cascade reaction involving the cyclization/oxygen-migration/ring-contraction process of 3-(beta, beta-diaryl) indolylethanol was disclosed. A variety of spiro 3,3'-cyclopropyl oxindole derivatives were efficiently synthesized in good yields under mild reaction conditions. A possible mechanism was suggested based on intermediate isolation and computational studies.

引用

页码：1141 / 1151

页数：11

共 50 条

[1] Asymmetric Synthesis of Spiro-3,3′-cyclopropyl Oxindoles via Vinylogous Michael Initiated Ring Closure Reaction
Manna, Abhijit
Joshi, Harshit
Singh, Vinod K.
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (24): : 16755 - 16766
[2] Synthesis of Spiro 3,3′-Cyclopropyl Oxindoles via Cyclopropanation of 3-Alkenyl-oxindoles with CF3-Imidoyl Sulfoxonium Ylides
Li, Chen
Zhang, Yu
Chen, Zhengkai
JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (10): : 3796 - 3804
[3] Synthesis of spiro-cyclics via ring-closing metathesis
Kotha, S
Manivannan, E
ARKIVOC, 2003, : 67 - 76
[4] Synthesis of Spiro-oxindoles (Spiroindolones) via Oxidative Ring Contraction Approach
Sharma, Yogesh Brijwashi
Sravani, Sattu
Hazra, Abhijit
CURRENT ORGANIC CHEMISTRY, 2023, 27 (15) : 1336 - 1346
[5] Progress towards the synthesis of shagene A via ring-closing metathesis cascade
Bai, Mengmeng
Wang, Xinyu
Li, Qi
TETRAHEDRON, 2024, 154
[6] Palladium-catalyzed direct arylation of cyclopropanes: Facile access to spiro 3,3′-cyclopropyl oxindoles
Ladd, Carolyn L.
Roman, Daniela Sustac
Charette, Andre B.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
[7] N-Bromosuccinimide-Mediated Radical Cyclization of 3-Arylallyl Azides: Synthesis of 3-Substituted Quinolines
Wang, Wei-Xia
Zhang, Qing-Zhao
Zhang, Tian-Qi
Li, Zhan-Shan
Zhang, Wei
Yu, Wei
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (01) : 221 - 226
[8] Synthesis of psudoheliotridane via formal [3+2] annulation and ring-closing metathesis
Chang, MY
Hsu, RT
Tseng, TW
Sun, PP
Chang, NC
TETRAHEDRON, 2004, 60 (26) : 5545 - 5550
[9] Ring-closing oleflin metathesis of 3,3′-(D-glycopyranosylidene)bis(1-propene) compounds as a route to anomeric spiro sugars
Chen, GR
Fei, ZB
Huang, XT
Xie, YY
Xu, JL
Gola, J
Steng, M
Praly, JP
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (15) : 2939 - 2946
[10] Discussion Addendum for: Ring-closing Metathesis Synthesis of N-Boc-3-pyrroline
O'Leary, Daniel J.
Pederson, Richard
Grubbs, Robert H.
ORGANIC SYNTHESES, 2012, 89 : 170 - 182

← 1 2 3 4 5 →