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

[21] Synthesis of Δ3-pyrrolines and Δ3-tetrahydropyridines via microwave-accelerated ring-closing metathesis
Grigg, R
Martin, W
Morris, J
Sridharan, V
TETRAHEDRON LETTERS, 2003, 44 (26) : 4899 - 4901
[22] Stereoselective synthesis of spiro[pyrrolidin-3,3′-oxindoles] via organocatalyzed asymmetric Mannich-type reaction
Shao, Hui
Huang, Xiu-Wu
Song, Lei
Zhou, Wen-Ting
Tang, Guan-Ping
Ye, Long
TETRAHEDRON LETTERS, 2018, 59 (32) : 3088 - 3093
[23] Facile, novel methodology for the synthesis of spiro[pyrrolidin-3,3′-oxindoles]:: Catalyzed ring expansion reactions of cyclopropanes by aldimines
Alper, PB
Meyers, C
Lerchner, A
Siegel, DR
Carreira, EM
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (21) : 3186 - 3189
[24] MICROWAVE-INDUCED N-BROMOSUCCINIMIDE-MEDIATED NOVEL SYNTHESIS OF PYRROLES VIA PAAL-KNORR REACTION
Andoh-Baidoo, Rosemarie
Danso, Robert
Mukherjee, Sanghamitra
Bandyopadhyay, Debasish
Banik, Bimal K.
HETEROCYCLIC LETTERS, 2011, 1 : 98 - 100
[25] Large-scale ring-closing metathesis synthesis of N-BOC-3-pyrroline.
Ferguson, ML
O'Leary, DJ
Grubbs, RH
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U139 - U139
[26] Synthesis of Spiro[piperidine-3,3′-oxindoles] via Gold(I)-Catalyzed Dearomatization of N-Propargyl- and N-Homoallenyl-2-bromotryptamines
Magne, Valentin
Blanchard, Florent
Marinetti, Angela
Voituriez, Arnaud
Guinchard, Xavier
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (21) : 3355 - 3361
[27] Biology-Oriented Synthesis of 3,3-Spiro(2-tetrahydrofuranyl)oxindoles
Murarka, Sandip
Golz, Christopher
Strohmann, Carsten
Antonchick, Andrey P.
Waldmann, Herbert
SYNTHESIS-STUTTGART, 2017, 49 (01): : 87 - 95
[28] Synthesis of Stapled β3-Peptides through Ring-Closing Metathesis
Bergman, Ylva E.
Del Borgo, Mark P.
Gopalan, Romila D.
Jalal, Sania
Unabia, Sharon E.
Ciampini, Marisa
Clayton, Daniel J.
Fletcher, Jordan M.
Mulder, Roger J.
Wilce, Jacqueline A.
Aguilar, Marie-Isabel
Perlmutter, Patrick
ORGANIC LETTERS, 2009, 11 (19) : 4438 - 4440
[29] Construction of spiro[pyrrolidine-3,3′-oxindoles] -: Recent applications to the synthesis of oxindole alkaloids
Marti, C
Carreira, EM
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (12) : 2209 - 2219
[30] Organocatalytic Synthesis of Spiro[pyrrolidin-3,3′-oxindoles] with High Enantiopurity and Structural Diversity
Chen, Xiao-Hua
Wei, Qiang
Luo, Shi-Wei
Xiao, Han
Gong, Liu-Zhu
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (38) : 13819 - 13825

← 1 2 3 4 5 →