The Reaction of Donor-Acceptor Cyclopropanes with 4,7-Dihydroindole: A New Protocol for the Synthesis of Divergent C2-Alkylated Indoles

被引：6

作者：

Kilic, Haydar ^{[1
,2
]}

Dalkilic, Oguzhan ^{[1
]}

机构：

[1] Ataturk Univ, Fac Sci, Dept Chem, TR-25240 Erzurum, Turkey

[2] Ataturk Univ, Oltu Vocat Training Sch, TR-25400 Erzurum, Turkey

来源：

CHEMISTRYSELECT | 2019年 / 4卷 / 13期

关键词：

4; 7-Dihydroindole; Donor-Acceptor Cyclopropane; Indole; p-Benzoquinone; Ytterbium(III) trifluoromethanesulfonate; FRIEDEL-CRAFTS ALKYLATION; DIRECT C2; ARYLATION; ACID;

D O I：

10.1002/slct.201900268

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nucleophilic ring opening reactions of donor-acceptor cyclopropanes with 4,7-dihydroindole (1 a) were described. A series of dimethyl 2-(2-(1H-indol-2-yl)-2-arylethyl)malonates were synthesized by using Ytterbium(III) trifluoromethanesulfonate as the catalyst for the first time in good to excellent yields. This study is also the first example for the reaction of donor-acceptor cyclopropanes with 4,7-dihydroindole. The obtained products are amenable to purposive elaborations. The synthesized compounds were characterized by using H-1 NMR, C-13 NMR and High Resolution Mass Spectroscopy (HRMS) techniques.

引用

页码：3737 / 3740

页数：4

共 2 条

[1] Ni(ClO4)2-Catalyzed Friedel-Crafts Reaction of Coumarin-Fused Donor-Acceptor Cyclopropanes with Indoles: Stereoselective Synthesis of trans-3,4-Disubstituted-3,4-dihydrocoumarins
Lee, Jusung
Ko, Kwang Min
Kim, Sung-Gon
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (30) : 4166 - 4170
[2] GaCl3-Catalyzed [3+2]-Cycloaddition/Esterification Cascade of Donor-Acceptor Cyclopropanes With Salicylaldehydes for the Synthesis of Tetrahydro-4H-Furo[3,2-c]Chromen-4-Ones
Liu, Zhiping
Pang, Jie
Che, Lijie
Gan, Chunfang
Cui, Jianguo
Huang, Yanmin
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, 61 (12) : 1953 - 1965

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