1,1′-Carbonyldiimidazole-mediated transformation of allomaltol containing hydrazides into substituted 3-acetyltetronic acids Full article
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Organic and Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539 |
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| Output data | Year: 2023, Volume: 21, Number: 35, Pages: 7224-7230 Pages count : 7 DOI: 10.1039/d3ob01136d | ||
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Abstract:
For the first time, the reaction of allomaltol containing hydrazides with 1,1′-carbonyldiimidazole (CDI) was studied. It was shown that under the considered conditions, 3-hydroxy-4-pyranone derivatives were transformed into 3-acetyltetronic acids bearing a pyrrolidin-2-one moiety. We have found that the key intermediates of the investigated process are substituted 6-oxa-1-azaspiro[4.5]dec-7-ene-2,9-diones. The structures of one final product and one intermediate were confirmed by X-ray analysis. The disclosed reaction was tested using a wide range of substituted allomaltols with various carboxamide units. It was demonstrated that in the case of hetaryl containing hydrazides and hydroxamic acids, the direction of the process is completely changed and cyclization into substituted pyrano[3,2-b]pyrans occurs.
Cite:
Komogortsev A.N.
, Lichitskii B.
, Melekhina V.
1,1′-Carbonyldiimidazole-mediated transformation of allomaltol containing hydrazides into substituted 3-acetyltetronic acids
Organic and Biomolecular Chemistry. 2023. V.21. N35. P.7224-7230. DOI: 10.1039/d3ob01136d WOS Scopus OpenAlex
1,1′-Carbonyldiimidazole-mediated transformation of allomaltol containing hydrazides into substituted 3-acetyltetronic acids
Organic and Biomolecular Chemistry. 2023. V.21. N35. P.7224-7230. DOI: 10.1039/d3ob01136d WOS Scopus OpenAlex
Identifiers:
| Web of science: | WOS:001055967600001 |
| Scopus: | 2-s2.0-85170675684 |
| OpenAlex: | W4386073152 |