Synthesis of 1,2,3-triazoles containing an allomaltol moiety from substituted pyrano[2,3-d]isoxazolones via base-promoted Boulton–Katritzky rearrangement

Synthesis of 1,2,3-triazoles containing an allomaltol moiety from substituted pyrano[2,3-d]isoxazolones via base-promoted Boulton–Katritzky rearrangement Full article

Journal

Beilstein Journal of Organic Chemistry
ISSN: 2195-951X , E-ISSN: 1860-5397

Output data

Year: 2024, Volume: 20, Pages: 1334-1340 Pages count : 7 DOI: 10.3762/bjoc.20.117

Authors

Milyutin Constantine Vyacheslavovich ¹ , Komogortsev Andrey Nikolaevich ¹ , Lichitsky Boris Valerievich ¹

Affiliations

1	Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation

For the first time, the interaction of aroyl containing pyrano[2,3-d]isoxazolone derivatives with various hydrazines was studied. It was shown that the considered process includes formation of corresponding hydrazones followed by Boulton–Katritzky rearrangement. As a result, the general method for the synthesis of substituted 1,2,3-triazoles bearing an allomaltol fragment was elaborated. The suggested approach can be applied to various aromatic and heterocyclic hydrazines. At the same time for unsubstituted hydrazine the Boulton–Katritzky recyclization is not implemented. In this case the opening of the pyranone ring was observed leading to pyrazolylisoxazole derivatives. Both types of aforementioned structures were proved by X-ray analysis.

Milyutin C.V. , Komogortsev A.N. , Lichitsky B.V.
Synthesis of 1,2,3-triazoles containing an allomaltol moiety from substituted pyrano[2,3-d]isoxazolones via base-promoted Boulton–Katritzky rearrangement
Beilstein Journal of Organic Chemistry. 2024. V.20. P.1334-1340. DOI: 10.3762/bjoc.20.117 WOS Scopus OpenAlex

Web of science:	WOS:001245868800001
Scopus:	2-s2.0-85196400316
OpenAlex:	W4399540510

DB	Citing
OpenAlex	4
Scopus	4
Web of science	4