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Updated: Jul 17, 2025

One-pot Microwave-assisted Conversion of Anomeric Nitrate-esters to Trichloroacetimidates
Published on: January 15, 2018
1,1'-Carbonyldiimidazole-mediated transformation of allomaltol containing hydrazides into substituted
Andrey N Komogortsev1, Boris V Lichitskii1, Valeriya G Melekhina1
1N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Leninsky Pr., 47, Moscow 119991, Russian Federation. dna5@mail.ru.
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.
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