Synthesis of Pyrrolo[2,1,5-cd]indolizine Rings via Visible-Light-Induced Intermolecular [3+2] Cycloaddition of Indolizines and Alkynes

被引：34

作者：

Zhang, Yu ^{[1
]}

Yu, Yue ^{[1
]}

Liang, Bing-bing ^{[1
]}

Pei, Yong-yan ^{[1
]}

Liu, Xiang ^{[1
]}

Yao, Hua-gang ^{[1
]}

Cao, Hua ^{[1
]}

机构：

[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Zhongshan 528458, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 16期

关键词：

FUNCTIONALIZATION; CONSTRUCTION; DERIVATIVES; CYCLIZATION; ARYLATION; ESTERS;

D O I：

10.1021/acs.joc.0c01253

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of indolizine smoothly underwent visible-light-induced intermolecular [3+2] annulations with internal alkynes to afford pyrrolo[2,1,5-cd]indolizine in good to excellent yields with high regioselectivity. Through this cascade reaction, a series of fluoroactive fused indolizines with a large pi-system were conveniently synthesized. The usage of visible light as energy source with air as a stoichiometric oxidant under simple conditions makes this process attractive and practical.

引用

页码：10719 / 10727

页数：9

共 44 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
Alberico, Dino
Scott, Mark E.
Lautens, Mark
[J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
[2] Design, Synthesis, and Functionalization of Imidazoheterocycles
Bagdi, Avik Kumar
Hajra, Alakananda
[J]. CHEMICAL RECORD, 2016, 16 (04) : 1868 - 1885
[3] Unexpected Inversions in Asymmetric Reactions: Reactions with Chiral Metal Complexes, Chiral Organocatalysts, and Heterogeneous Chiral Catalysts
Bartok, Mihaly
[J]. CHEMICAL REVIEWS, 2010, 110 (03) : 1663 - 1705
[4] Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C-H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides
Bellina, Fabio
Rossi, Renzo
[J]. CHEMICAL REVIEWS, 2010, 110 (02) : 1082 - 1146
[5] Can silicon substituted metal-free organic dyes achieve better efficiency compared to silicon free organic dyes? A computational study
Biswas, Abul Kalam
Das, Amitava
Ganguly, Bishwajit
[J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2015, 17 (46) : 31093 - 31100
[6] Visible Light-Induced and Singlet Oxygen-Mediated Photochemical Conversion of 4-Hydroxy-α-benzopyrones to 2-Hydroxy-3-oxo-2,3-dihydrobenzofuran-2-carboxamides/carboxylates Using Rose Bengal as a Photosensitizer
Brahmachari, Goutam
Karmakar, Indrajit
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (14) : 8851 - 8864
[7] Gold-Catalyzed Cycloisomerization of Pyridine-Bridged 1,8-Diynes: An Expedient Access to Luminescent Cycl[3.2.2]azines
Chintawar, Chetan C.
Mane, Manoj V.
Tathe, Akash G.
Biswas, Suprakash
Patil, Nitin T.
[J]. ORGANIC LETTERS, 2019, 21 (17) : 7109 - 7113
[8] Nitrogen-Centered Concave Molecules with Double Fused Pentagons
Deng, Niping
Zhang, Gang
[J]. ORGANIC LETTERS, 2019, 21 (13) : 5248 - 5251
[9] Selective photocatalytic reactions with organic photocatalysts
Fukuzumi, Shunichi
Ohkubo, Kei
[J]. CHEMICAL SCIENCE, 2013, 4 (02) : 561 - 574
[10] FORMATION OF CYCL[3.2.2]AZINE DERIVATIVES VIA REACTION OF PYRROCOLINE WITH DIMETHYL ACETYLENEDICARBOXYLATE
GALBRAITH, A
BARNES, RA
SMALL, T
BOEKELHEIDE, V
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (02) : 453 - &

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