Multicomponent synthesis of allomaltol containing 2-aminooxazoles and acid-catalyzed recyclization into substituted furo[3,2-b]pyrans

Komogortsev, Andrey N.; Lichitsky, Boris V.; Karibov, Turan T.; Melekhina, Valeriya G.

doi:10.1016/j.tet.2022.132836

Cited by 4 publications

(3 citation statements)

References 28 publications

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“…The formation of the 2-aminooxozole core as opposed to a urea-containing condensed furan was the distinctive feature of this approach (Scheme 72). 92…”

Section: Use Of Aryl Glyoxal In Designing O-heterocycles Using Multic...mentioning

confidence: 99%

Aryl glyoxal: a prime synthetic equivalent for multicomponent reactions in the designing of oxygen heterocycles

2023

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“…The formation of the 2-aminooxozole core as opposed to a urea-containing condensed furan was the distinctive feature of this approach (Scheme 72). 92…”

Section: Use Of Aryl Glyoxal In Designing O-heterocycles Using Multic...mentioning

confidence: 99%

Aryl glyoxal: a prime synthetic equivalent for multicomponent reactions in the designing of oxygen heterocycles

2023

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“…Previously, the methods for the synthesis of a wide range of terarylenes containing an allomaltol fragment were developed in our group [21][22][23][24][25][26]. Ongoing the research in this area, herein, we studied the reaction of aroyl containing substituted pyrano [2,3-d]isoxazolones 1 with various hydrazine hydro-chlorides 2.…”

Section: Introductionmentioning

confidence: 99%

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

Milyutin,

Komogortsev,

Lichitsky

2024

Beilstein J. Org. Chem.

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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.

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“…Previously, we have elaborated various synthetic methods for the preparation of wide range of products containing 3‐hydroxy‐4‐pyranone (allomaltol) fragment [11]. At the same time, the use of acidic media allows one to perform a number of original transformations for allomaltol derivatives [12].…”

Section: Introductionmentioning

confidence: 99%

Acid‐catalyzed recyclization of spiroindolinepyrano[3,2‐b]pyrans to 3,4‐dihydroquinolinone derivatives containing allomaltol fragment

Milyutin

Komogortsev

Lichitsky

et al. 2023

Journal of Heterocyclic Chem

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For the first time, we developed a novel one‐step method for the synthesis of substituted 3,4‐dihydroquinolinones with allomaltol moiety. The suggested approach includes acid‐catalyzed recyclization of spiroindolinepyrano[3,2‐b]pyrans which can be obtained by multicomponent reaction of 3‐hydroxy‐4‐pyranones, isatins and malononitrile. The described transformation is a distinctive feature of 3‐hydroxy‐4‐pyranone derivatives and is not typical for other heterocyclic enols. The advantages of the considered method are the employment of easily accessible starting materials and simple work‐up procedure which can avoid chromatographic purification. The structure of one of synthesized products was determined by x‐ray diffraction.

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Multicomponent synthesis of allomaltol containing 2-aminooxazoles and acid-catalyzed recyclization into substituted furo[3,2-b]pyrans

Cited by 4 publications

References 28 publications

Aryl glyoxal: a prime synthetic equivalent for multicomponent reactions in the designing of oxygen heterocycles

Aryl glyoxal: a prime synthetic equivalent for multicomponent reactions in the designing of oxygen heterocycles

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

Acid‐catalyzed recyclization of spiroindolinepyrano[3,2‐b]pyrans to 3,4‐dihydroquinolinone derivatives containing allomaltol fragment

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