Synthesis of Benzalacetophenone-based Isoxazoline and Isoxazole Derivatives

Abstract

The demand for natural product based drugs with less cost and efficient procedures has become a challenge to researchers. Benzalacetophenone is a natural product based species that is modified into numerous heterocyclic compounds including isoxazoline and isoxazole derivatives. The utility of isoxazoline and oxazole derivatives has been increased for the synthesis of the new and effective chemical entities to serve medicinal chemistry in the past few years. Isoxazoline and isoxazole are fascinating classes of heterocyclic compounds, which belong to N- and O-heterocycles, and are widely used as precursors for the development of drugs. This review highlights the recent work for the synthesis of mono and bis isoxazoline and isoxazole derivatives using stable benzalacetophenone and functionalization of isoxazoline and isoxazole, along with the prevailing biological properties.

Nitrile Oxide, Alkenes, Dipolar Cycloaddition, Isomerization and Metathesis Involved in the Syntheses of 2-Isoxazolines

“…In the review from 2022, the recent advances in the synthesis of isoxazolines from Ar 1 COCH=CHAr 2 are presented— Scheme 288 [ 319 ].…”

“… Synthesis of 3,5-disubstituted isoxazolines from Ar 1 COCH=CHAr 2 [ 319 ]. Ar 1 , Ar 2 = Ph, substituted Ph, naphthyl, heteroaryl; a = NH 2 OH or NH 2 OH·HCl, solvent (EtOH, AcOH, and others), various conditions.…”

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

“…They may also exhibit completely different biological activities from the parent [ 23 ]. Given the importance of the isoxazole/isoxazoline backbone in natural products and the remarkable bioactivity, an increasing number of studies have reported the modification of natural products by isoxazole/isoxazoline rings [ 24 ]. A number of research groups have intensively studied this field; therefore, this paper presents the progress of this field in conjunction with the latest literature reports.…”

N-heterocyclic carbene-catalyzed direct enantioselective synthesis of dihydroisoxazolo[5,4-b]pyridin-6-ones

“…Isoxazole, a five-membered-ring heterocyclic compound bearing both nitrogen and oxygen atoms, is a privileged skeleton in medicinal chemistry due to its diverse biological activities related to the structure. 1 Among its derivatives, 5-amino-isoxazole not only widely exists in a large variety of pharmacologically active molecules but also serves as a versatile building block in organic synthesis. 2 In this context, various functionalized heterocycles containing 5-aminoisoxazole moieties have been synthesized.…”