Mechanochemical synthesis of coumarins via Pechmann condensation under solvent-free conditions: an easy access to coumarins and annulated pyrano[2,3-f] and [3,2-f]indoles

被引：19

作者：

Sharapov, Ainur D. ^{[1
]}

Fatykhov, Ramil F. ^{[1
]}

Khalymbadzha, Igor A. ^{[1
,2
]}

Sharutin, Vladimir V. ^{[3
]}

Santra, Sougata ^{[1
]}

Zyryanov, Grigory, V ^{[1
,2
]}

Chupakhin, Oleg N. ^{[1
,2
]}

Ranu, Brindaban C. ^{[4
]}

机构：

[1] Ural Fed Univ, Chem Engn Inst, Dept Organ & Biomol Chem, Ekaterinburg 620002, Russia

[2] Russian Acad Sci, Inst Organ Synth, Ural Branch, Ekaterinburg 620219, Russia

[3] South Ural State Univ, Inst Nat Sci, Dept Chem, Chelyabinsk 454080, Russia

[4] Indian Assoc Cultivat Sci, Sch Chem Sci, Kolkata 700032, India

来源：

GREEN CHEMISTRY | 2022年 / 24卷 / 06期

基金：

俄罗斯科学基金会;

关键词：

BIOLOGICAL EVALUATION; POLYMER MECHANOCHEMISTRY; DERIVATIVES; GREEN; EFFICIENT; DESIGN; CATALYST; ACID; INDOLES; ANALOGS;

D O I：

10.1039/d1gc04564d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A green protocol has been developed for the synthesis of simple coumarins and linear pyrano[2,3-f] and [3,2-f]indoles by the reaction of phenol derivatives with beta-ketoesters under ball milling at ambient temperature in the presence of methanesulfonic acid as a mild acid catalyst. The significant advantages of this procedure are high yields, scalability, no use of hazardous acids or solvents, shorter reaction time, ambient temperature, low cost, and straightforward purification without column chromatography. This procedure is associated with high EcoScale metrics and a low E-factor. In contrast to traditional Pechmann condensation procedures, the mechanochemical protocol leads to the synthesis of pyranoindoles with excellent regioselectivity and high yields.

引用

页码：2429 / 2437

页数：9

共 28 条

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