Tandem one-pot synthesis of flavans by recyclable silica-HClO4 catalyzed Knoevenagel condensation and [4+2]-Diels-Alder cycloaddition

被引：36

作者：

Bharate, Sandip B. ^{[1
]}

Mudududdla, Ramesh ^{[1
]}

Bharate, Jaideep B. ^{[1
]}

Battini, Narsaiah ^{[1
]}

Battula, Satyanarayana ^{[1
]}

Yadav, Rammohan R. ^{[1
]}

Singh, Baldev ^{[2
]}

Vishwakarma, Ram A. ^{[1
]}

机构：

[1] Indian Inst Integrat Med CSIR, Div Med Chem, Jammu 180001, India

[2] Indian Inst Integrat Med CSIR, Natl Prod Chem Div, Jammu 180001, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 26期

关键词：

GREEN TEA CATECHINS; BIOMIMETIC SYNTHESIS; HETEROGENEOUS CATALYST; EFFICIENT; DEHYDROGENATION; INHIBITION; ALCOHOLS; BINDING;

D O I：

10.1039/c2ob25376c

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

An efficient one-pot multi-component synthesis of flavans using perchloric acid supported on silica as a recyclable heterogeneous catalyst has been described. This is the first report of direct one-step construction of a flavan skeleton from a phenolic precursor. The method involves a Knoevenagel-type condensation leading to in situ formation of transient O-quinone methide which further undergoes [4 + 2]-Diels-Alder cycloaddition with styrene to yield a flavan skeleton. The method provides easy access to a wide range of bio-active natural products viz. flavonoids, anthocyanins and catechins.

引用

页码：5143 / 5150

页数：8

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