A formal vinylic substitution reaction for the synthesis of α,β-unsaturated enol esters and their anticancer potential

被引：0

作者：

Swami, Bhawna ^{[1
]}

Kumari, Neetu ^{[2
]}

Maruthi, Mulaka ^{[2
]}

Kunjunny, Neethu K. ^{[3
]}

Menon, Rajeev S. ^{[3
]}

机构：

[1] Cent Univ Haryana, Dept Chem, Mahendergarh 123031, Haryana, India

[2] Cent Univ Haryana, Dept Biochem, Mahendergarh 123031, Haryana, India

[3] Univ Calicut, Dept Chem, Malappuram 673635, Kerala, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 16期

关键词：

SULFONES; CYCLIZATION; SOLVOLYSIS; DERIVATIVES;

D O I：

10.1039/d4ob00401a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arylsulfonyl group-bearing alpha,beta-unsaturated enol esters were readily assembled via the Cs2CO3-mediated union of 2-bromoallyl sulfones and cinnamic acids. The overall transformation is equivalent to an sp2 carbon-oxygen coupling reaction, and therefore constitutes a formal vinylic substitution. Several of the products display promising levels of antiproliferative activities higher than that of the anticancer drug carboplatin. Thiophenol reacted with 2-bromoallyl sulfones under identical conditions to afford alpha-thiophenyl-alpha '-tosyl acetone via an apparent aerial oxidation. Cesium carbonate promoted a 'formal vinylic substitution' of the bromine in 2-bromoallyl sulfones by alpha,beta-unsaturated acids. The arylsulfonyl group-bearing enol esters thus produced displayed promising levels of anticancer activity.

引用

页码：3273 / 3278

页数：6

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