Formal (3+4)-Annulation of Propargylic p-Quinone Methides with 2-Indolylmethanols: Synthesis of Polysubstituted Indole-Fused Oxepines

被引：21

作者：

Qiu, Zong-Wang ^{[1
]}

Li, Bao Qiong ^{[1
]}

Liu, Hong-Fu ^{[1
]}

Zhu, Zhi-Qiang ^{[1
]}

Pan, Han-Peng ^{[1
]}

Feng, Na ^{[1
]}

Ma, Ai-Jun ^{[1
]}

Peng, Jin-Bao ^{[1
]}

Zhang, Xiang-Zhi ^{[1
]}

机构：

[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Guangdong, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 11期

关键词：

STRATEGIES;

D O I：

10.1021/acs.joc.1c00484

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Bronsted acid catalyzed 1,8-addition mediated (3 + 4)-annulation of in situ generated propargylic p-quinone methides with 2-indolylmethanols is described. This method provides a convenient and mild approach to structurally interesting and synthetically important polysubstituted indole-fused oxepines in high yields. Moreover, 2-indolylmethanols as four-atom synthons in the (3 + 4)-annulations under Bronsted acid conditions have been explored for the first time.

引用

页码：7490 / 7499

页数：10

共 44 条

[1] Synthesis of indole-fused scaffolds via [3+3] cyclization reaction of 2-indolylmethanols with quinone imines
Qin, Lu-Zhe
Cheng, Ya-Long
Wen, Xiaoan
Xu, Qing-Long
Zhen, Le
TETRAHEDRON, 2021, 77
[2] Construction of heterocycle-fused tetrahydrocarbazoles through a formal [3+3]-annulation of 2-indolylmethanols with para-quinone methides
Singh, Gurdeep
Sharma, Sonam
Pandey, Rajat
Rekha
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ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (12) : 2493 - 2498
[3] Catalytic Asymmetric [4+3] Cyclizations of 2-Indolylmethanols with ortho-Quinone Methides
Liu, Lu
Zhang, Junliang
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (11) : 3308 - 3309
[4] Catalytic Asymmetric (4+3) Cyclizations of In Situ Generated ortho-Quinone Methides with 2-Indolylmethanols
Sun, Meng
Ma, Chun
Zhou, Si-Jia
Lou, Sai-Fan
Xiao, Jian
Jiao, Yinchun
Shi, Feng
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (26) : 8703 - 8708
[5] Metal-Catalyzed Regiospecific (4+3) Cyclization of 2-Indolylmethanols withortho-Quinone Methides
Zhou, Si-Jia
Sun, Meng
Wang, Jing-Yi
Yu, Xian-Yang
Lu, Han
Zhang, Yu-Chen
Shi, Feng
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (28) : 4301 - 4308
[6] High diastereoselective [4+2] annulation of β,γ-unsaturated α-keto esters and p-quinone methides: Approach to polysubstituted 4-aryl chromans and tetrahydroquinolines
Si, Wen
Xu, Fan
Liu, Zhanxu
Song, Ran
Lv, Jian
TETRAHEDRON LETTERS, 2020, 61 (31)
[7] Synthesis of Naphthopyrans via Formal (3+3)-Annulation of Propargylic (Aza)-para-Quinone Methides with Naphthols
Zhang, Xiang-Zhi
Li, Bao Qiong
Qiu, Zong-Wang
Ma, Ai-Jun
Peng, Jin-Bao
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Feng, Na
Xu, Xue-Tao
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JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (20): : 13306 - 13316
[8] Diastereoselective Synthesis of Tetrahydroquinolines via [4+2] Annulation between in Situ Generated p-Quinone Methides and Nitroalkenes
Wang, Junwei
Pan, Xiang
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ORGANIC LETTERS, 2018, 20 (19) : 5995 - 5998
[9] One-pot formal [3+2] annulation of 2-pyridinyl-substituted p-quinone methides and arynes for the synthesis of 3-aryl pyrido[1,2-a]indoles
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[10] Palladium-Catalyzed Asymmetric (2+3) Annulation of p-Quinone Methides with Trimethylenemethanes: Enantioselective Synthesis of Functionalized Chiral Spirocyclopentyl p-Dienones
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An, Xian-Tao
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ORGANIC LETTERS, 2020, 22 (11) : 4171 - 4175

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