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

被引：3

作者：

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

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

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

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

Wang, Zhaobo ^{[1
,2
,3
]}

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

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

Cheng, Maosheng ^{[1
,2
,3
]}

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

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 09期

基金：

中国国家自然科学基金;

关键词：

HOMOGENEOUS GOLD CATALYSIS; INDUSTRIAL PERSPECTIVE; TANDEM CYCLIZATIONS; INDOLE ALKALOIDS; COUNTER ANIONS;

D O I：

10.1021/acs.joc.2c03104

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Density functional theory calculations were applied to predict the pathways of gold(I)-catalyzed cycloisomerization of the indole substrates with 1,6-enynes, which were consistent with the ensuing experimental results. The substitution-controlled synthesis led to the formation of 1H-pyrido[4,3-b]indole and spiro[indoline-3,3 '-pyridine] derivatives in a tunable way. The reactions had good functional group tolerances, and a possible mechanism was proposed based on the computational and experimental results.

引用

页码：5483 / 5496

页数：14

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