5-硝基异恶唑在 SAr 反应中的应用：多取代异恶唑衍生物的合成。

5-Nitroisoxazoles in SAr reactions: access to polysubstituted isoxazole derivatives.

机构信息

Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russia.

Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, Moscow 119991, Russia and IPhaC RAS, Severnyi Proezd, 1, Chernogolovka, Moscow Region 142432, Russia.

出版信息

Org Biomol Chem. 2021 Jul 28;19(29):6447-6454. doi: 10.1039/d1ob00816a.

DOI:10.1039/d1ob00816a

PMID:34236067

Abstract

An efficient protocol for the straightforward functionalization of the isoxazole ring via the reactions of aromatic nucleophilic substitution of the nitro group with various nucleophiles has been elaborated. The method features excellent chemical yields, easy operability of the reaction, mild reaction conditions and a broad scope of both 5-nitroisoxazoles and nucleophiles. A synthetic approach to 3,5- and 3,4,5-substituted isoxazoles via the sequential functionalization of the isoxazole ring has been developed based on the excellent regioselectivity of the reaction of 3,5-dinitroisoxazoles with nucleophiles.

摘要

已经详细阐述了一种通过各种亲核试剂对硝基基团的芳香亲核取代反应来直接官能化异恶唑环的有效方法。该方法具有出色的化学收率、反应的易操作性、温和的反应条件以及 5-硝基异恶唑和亲核试剂的广泛范围。基于 3,5-二硝基异恶唑与亲核试剂反应的优异区域选择性，开发了一种通过异恶唑环的顺序官能化来合成 3,5-和 3,4,5-取代异恶唑的方法。