Gold(I)-Catalyzed Substitution-Controlled Syntheses of Spiro[indoline-3,3′-pyrrolidine] and Spiro[indoline-3,3′-piperidine] Derivatives

被引：1

作者：

Zhu, Jiang ^{[1
,2
,3
]}

Li, Jiaji ^{[1
,2
,3
]}

Zhang, Lianjie ^{[1
,2
,3
]}

Sun, Shitao ^{[1
,2
,3
]}

Yang, Lu ^{[1
,2
,3
]}

Fu, Jiayue ^{[1
,2
,3
]}

Sun, Hanyang ^{[1
,2
]}

Cheng, Maosheng ^{[1
,2
]}

Lin, Bin ^{[1
,2
,3
]}

Liu, Yongxiang ^{[1
,2
,3
]}

机构：

[1] Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, Shenyang 110016, Peoples R China

[2] Inst Drug Res Med Capital China, Benxi 117000, Peoples R China

[3] Shenyang Pharmaceut Univ, Wuya Coll Innovat, Shenyang 110016, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 15期

基金：

中国国家自然科学基金;

关键词：

GOLD-CATALYZED CYCLOISOMERIZATION; INDUSTRIAL PERSPECTIVE; COUNTER ANIONS; CYCLIZATION; SPIROINDOLENINES; DEAROMATIZATION; REGIODIVERGENT; SELECTIVITY; INDOLES; ALKYNES;

D O I：

10.1021/acs.joc.3c00604

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Spiro[indoline-3,3 & PRIME;-pyrrolidine]and spiro[indoline-3,3 & PRIME;-piperidine] derivativeswere synthesized in a substitution-controlledmanner under the catalysis of cationic gold(I) species in the presenceof Hantzsch ester (HEH). The optimal reaction condition was determinedby screening, and the functional group tolerances of these two pathwayswere examined by readily synthetic substrates. The endo and exo selectivities of these cyclizations wereelucidated by density functional theory calculations, and a plausiblemechanism for these transformations was proposed.

引用

页码：10586 / 10598

页数：13

共 15 条

[1] Quantum Mechanical Prediction and Experimental Verification of Au(I)-Catalyzed Substitution-Controlled Syntheses of 1H-Pyrido[4,3-b]indole and Spiro[indoline-3,3?-pyridine] Derivatives
Zhu, Jiang
Li, Jiaji
Zhang, Lianjie
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JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09) : 5483 - 5496
[2] An Organocatalytic Cascade Spirocycloaddition Reaction for the Construction of Spiro[indoline-3,3′-piperidin]-6′-ones
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[7] Silver Triflate/N-Fluorobenzenesulfonimide-Catalyzed Cycloisomerization of Tryptamine-Ynamide to Spiro[indoline-3,4′-piperidine] Induced by Cation-π-π Interactions between Substrate and Metal Ligand
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[8] Convenient construction of spiro[indoline-3,5′-pyrrolo[3,4-c]carbazole] and spiro[indene-2,5′-pyrrolo[3,4-c]carbazole] via acid-catalyzed Diels-Alder reaction
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[9] Copper-Catalyzed Trifluoromethylation of Acrylamides Coupled with Indole Dearomatization: Access to Trifluoromethyl-Substituted Spiro[indole-3,3′-pyrrolidine] Derivatives
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[10] Efficient synthesis of functionalized spiro[indoline-3,4′-pyrrolo[3,4-b]pyridines] via one-pot three-component reaction
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