Study of the interaction of 2H-furo[3,2-b]pyran-2-ones with nitrogen-containing nucleophiles
Constantine V Milyutin, Andrey N Komogortsev, Boris V Lichitsky
TL;DR
This study explores how certain chemical compounds react with nitrogen-based molecules, leading to new methods for synthesizing specific ring structures.
Contribution
The paper introduces a new general method for synthesizing substituted pyrazol-3-ones containing the allomaltol fragment.
Findings
Reactions with aliphatic amines produce 2H-furo[3,2-b]pyran-2,7(3H)-diones with exocyclic enamine groups.
Dinucleophiles cause recyclization and furan ring opening, enabling synthesis of pyrazol-3-ones.
X-ray diffraction confirmed the structures of all synthesized products.
Abstract
For the first time, the reaction of substituted 2H-furo[3,2-b]pyran-2-ones with diverse N-nucleophiles was investigated. It was shown that the direction of the process depends on the type of employed nitrogen-containing reagent. For example, condensation with aliphatic amines leads to 2H-furo[3,2-b]pyran-2,7(3H)-diones bearing an exocyclic enamine moiety. At the same time, interaction with dinucleophiles results in recyclization accompanied by opening of the furan ring. Relied on the aforementioned process a general method for the synthesis of substituted pyrazol-3-ones with allomaltol fragment was designed. Structures of representatives of all obtained products were unambiguously confirmed by X-ray diffraction.
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Taxonomy
TopicsSynthesis of Organic Compounds · Organic Chemistry Synthesis Methods · Synthesis and Reactions of Organic Compounds