Synthesis of Indolyl-Tethered Spiro[cyclobutane-1,1′-indenes] through Cascade Reactions of 1-(Pyridin-2-yl)-1H-indoles with Alkynyl Cyclobutanols

被引：17

作者：

Xu, Yuanshuang ^{[1
]}

Yu, Caiyun ^{[1
]}

Zhang, Xinying ^{[1
]}

Fan, Xuesen ^{[1
]}

机构：

[1] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, Sch Chem & Chem Engn,Minist Educ, NMPA Key Lab Res & Evaluat Innovat Drug,Key Lab G, Xinxiang 453007, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 21期

基金：

中国国家自然科学基金;

关键词：

C-H FUNCTIONALIZATION; ANNULATION; ALKENYLATION; ACTIVATION; DERIVATIVES; STRATEGY; CATALYST; BIRDS;

D O I：

10.1021/acs.orglett.1c03200

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Presented herein is an efficient and unprecedented synthesis of indolyl-tethered spiro[cyclobutane-1,1'-indenes] through the cascade reaction of 1-(pyridin-2-yl)-1H-indoles with alkynyl cyclobutanols. Mechanistic experiments implicate a sequential process in which 1-(pyridin-2-yl)-1H-indole first undergoes an alkenylation with alkynyl cyclobutanol followed by an intramolecular Friedel-Crafts reaction to give the title products. The utility of this novel protocol was reflected by the ample substrate scope, high chemo- and regioselectivity, removable directing group, and scalable preparation. In addition, the product thus obtained can be further derivatized quite efficiently.

引用

页码：8510 / 8515

页数：6

共 39 条

[1] An entry to 2-(cyclobut-1-en-1-yl)-1H-indoles through a cyclobutenylation/deprotection cascade
Natho, Philipp
Yang, Zeyu
Allen, Lewis A. T.
Rey, Juliette
White, Andrew J. P.
Parsons, Philip J.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (18) : 4048 - 4053
[2] 1-[(Imidazolidin-2-yl)imino]-1H-indoles as new hypotensive agents: synthesis and in vitro and in vivo biological studies
Kornicka, Anita
Wasilewska, Aleksandra
Saczewski, Jaroslaw
Hudson, Alan L.
Boblewski, Konrad
Lehmann, Artur
Gzella, Karol
Belka, Mariusz
Saczewski, Franciszek
Gdaniec, Maria
Rybczynska, Apolonia
Baczek, Tomasz
CHEMICAL BIOLOGY & DRUG DESIGN, 2017, 89 (03) : 400 - 410
[3] Rh/Cu-catalyzed multiple C-H, C-C, and C-N bond cleavage: facile synthesis of pyrido[2,1-a]indoles from 1-(pyridin-2-yl)-1H-indoles and γ-substituted propargyl alcohols
Li, Ting
Wang, Zhen
Zhang, Mingliang
Zhang, Hui-Jun
Wen, Ting-Bin
CHEMICAL COMMUNICATIONS, 2015, 51 (31) : 6777 - 6780
[4] SYNTHESIS OF 3-(1,2,3,6-TETRAHYDRO PYRIDIN-4-YL) 1H-INDOLES AND STUDY OF THEIR SEROTONINERGIC AND ANTIDOPAMINERGIC PROPERTIES
GUILLAUME, J
DUMONT, C
LAURENT, J
NEDELEC, L
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1987, 22 (01) : 33 - 43
[5] Synthesis, Crystal Structure and Biological Activity of Novel 1-(Pyridin-2-yl)-2-aryloxy-2-(1H-1,2,4-triazol-1-yl)ethanones
Dai, Hong
Liu, Jianbing
Tao, Weifeng
Miao, Wenke
Fang, Jianxin
Wang, Qingmin
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (02) : 393 - 398
[6] Synthesis of Potential Anticancer 1-(1H-Indol-3-yl)isoquinolines by Silver Nitrate Mediated Tandem Reactions of 2-Alkynyl-benzaldehyde Azines and Indoles
Zhao, Yun-Hui
Luo, Yueyang
Zhu, Yingli
Wang, Hang
Zhou, Hangbin
Tan, Hailong
Zhou, Zhihua
Ma, Yong-Cheng
Xie, Wenlin
Tang, Zilong
SYNLETT, 2018, 29 (06) : 773 - 778
[7] Synthesis of annulated bis-indoles through Au(I)/Bronsted acid-catalyzed reactions of (1H-indol-3-yl)(aryl)methanols with 2-(arylethynyl)-1H-indoles
Inamdar, Suleman M.
Gonnade, Rajesh G.
Patil, Nitin T.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (04) : 863 - 869
[8] Cp*Co(III)-Catalyzed Regioselective Synthesis of Cyclopenta[b]carbazoles via Dual C(sp2)-H Functionalization of 1-(Pyridin-2-yl)-indoles with Diynes
Li, Qiuyun
Wang, Yanwei
Li, Bin
Wang, Baiquan
ORGANIC LETTERS, 2018, 20 (24) : 7884 - 7887
[9] Ambient-Temperature Synthesis of (E)-N-(3-(tert-Butyl)-1-methyl-1H-pyrazol-5-yl)-1-(pyridin-2-yl)methanimine
Becerra, Diana
Cobo, Justo
Castillo, Juan-Carlos
MOLBANK, 2021, 2021 (03)
[10] Crystal structures of (E)-5-(4-methylphenyl)-1-(pyridin-2-yl)pent-2-en-4-yn-1-one and [3,4-bis-(phenylethynyl)cyclobutane-1,2-diyl]bis(pyridin-2-ylmethanone)
Ushakov, Ivan E.
Odin, Ivan S.
Gloukhov, Pavel A.
Golovanov, Alexander A.
Dorovatovskii, Pavel V.
Vologzhanina, Anna V.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2020, 76 : 192 - +

← 1 2 3 4 →