Abstract: Alkynones have gained great attention as useful building blocks in organic synthesis. They have been emerged as key intermediates in the synthesis of various heterocycles. In the present study, the alkynylketones derived from antranylic acids esters or alkaloid lappaconitine were employed as a platform for late-stage derivatisation. The synthesis of regioisomeric 3,5-diarylisoxazoles was achieved starting from ethyl N-acetyl-5-iodoanthranilate. A range of 3,5-disubstituted isoxazoles, containing the plant alkaloid lappaconitine moiety at the C-3 position were convenience synthesized by a consecutive three-component alkynylation-cyclocondensation sequence starting from of 5 '-ethynyllappaconitine, aroyl chlorides, and hydroxylamine hydrochloride. Notably, several 5-hydroxy-4,5-dihydroisoxazoles were obtained in good yields as main products in this three component reaction by using Et3N as the base and i-PrOH as the solvent in cyclocondensation step.

Cite: Cheremnykh K.P. , Savelyev V.A. , Shults E.E.
An Efficient Access to 3,5-Disubstituted Isoxazoles with Anthranilate Ester Moiety: Alkaloid Lappaconitine - Aryl Conjugates with an Isoxazole Linker
Asian Journal of Organic Chemistry. 2021. V.10. N10. P.2638-2643. DOI: 10.1002/ajoc.202100474 WOS Scopus

Identifiers:

Web of science	WOS:000700950000001
Scopus	2-s2.0-85115856028
OpenAlex	W3204269777

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