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铜催化的乙烯基叠氮化物和苄胺的氧化级联脱氨/环化反应合成 2,4,6-三芳基吡啶。

Copper catalysed oxidative cascade deamination/cyclization of vinyl azide and benzylamine for the synthesis of 2,4,6-triarylpyridines.

机构信息

Department of Industrial and Engineering Chemistry, Institute of Chemical Technology, Indian Oil Odisha Campus, Samantpuri, Bhubaneswar 751013, India.

Department of Humanities and Sciences, Vardhaman College of Engineering, Shamshabad, Hyderabad-501218, Telangana, India.

出版信息

Org Biomol Chem. 2023 Jul 5;21(26):5419-5423. doi: 10.1039/d3ob00625e.

Abstract

A highly efficient one-pot method for the synthesis of 2,4,6-triaryl pyridines has been developed cascade deamination and annulation. Copper triflate and molecular iodine easily promoted the oxidative cyclization reaction of vinyl azide and benzylamine to access a wide variety of substituted pyridine substrates under an oxygen atmosphere. The presence of benzyl amine enables the cyclization process by providing the aryl functionality and the nitrogen source. Moreover, a broad range of substrates with good functional group tolerance, avoidance of external oxidants, excellent product yields, operational simplicity and mild conditions are the notable advantages of the present protocol.

摘要

发展了一种高效的一锅法,通过脱氨和环化级联反应合成 2,4,6-三芳基吡啶。三氟甲磺酸铜和分子碘容易促进乙烯基叠氮化物和苄胺的氧化环化反应,在氧气气氛下,以多种取代的吡啶底物为底物。苄胺的存在通过提供芳基官能团和氮源使环化过程成为可能。此外,本方法具有广泛的底物适用性、良好的官能团耐受性、避免使用外部氧化剂、产率高、操作简单、条件温和等显著优点。

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