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

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

Journal

Journal of Heterocyclic Chemistry
ISSN: 0022-152X , E-ISSN: 1943-5193

Output data

Year: 2023, Volume: 60, Number: 8, Pages: 1427-1436 Pages count : 10 DOI: 10.1002/jhet.4690

Authors

Milyutin Constantine V. ¹ , Komogortsev Andrey N. ¹ , Lichitsky Boris V. ¹ , Melekhina Valeriya G. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Science, Moscow, Russia

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.

Milyutin C.V. , Komogortsev A.N. , Lichitsky B.V. , Melekhina V.G.
Acid‐catalyzed recyclization of spiroindolinepyrano[3,2‐b]pyrans to 3,4‐dihydroquinolinone derivatives containing allomaltol fragment
Journal of Heterocyclic Chemistry. 2023. V.60. N8. P.1427-1436. DOI: 10.1002/jhet.4690 WOS Scopus OpenAlex

Web of science:	WOS:001000029900001
Scopus:	2-s2.0-85161461182
OpenAlex:	W4379143546

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