One-pot synthesis of substituted pyrrolo[3,4-b]pyridine-4,5-diones based on the reaction of N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines

One-pot synthesis of substituted pyrrolo[3,4-b]pyridine-4,5-diones based on the reaction of N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines Full article

Journal

Beilstein Journal of Organic Chemistry
ISSN: 2195-951X , E-ISSN: 1860-5397

Output data

Year: 2019, Volume: 15, Pages: 2840-2846 Pages count : 7 DOI: 10.3762/bjoc.15.277

Authors

Melekhina Valeriya G ¹ , Komogortsev Andrey N ¹ , Lichitsky Boris V ¹ , Mityanov Vitaly S ^2,1 , Fakhrutdinov Artem N ¹ , Dudinov Arkady A ¹ , Migulin Vasily A ¹ , Nelyubina Yulia V ³ , Melnikova Elizaveta K ^4,3 , Krayushkin Michail M ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian academy of sciences, Leninsky pr. 47, Moscow, 119991, Russian Federation
2	Department of Fine Organic Synthesis and Chemistry of Dyes, D. Mendeleyev University of Chemical Technology of Russia, Miusskaya Sq., 9, Moscow 125047, Russian Federation
3	A. N. Nesmeyanov Institute of Organoelement Compounds, Vavilova St., 28, Moscow 119991, Russian Federation.
4	Lomonosov Moscow State University, Moscow 119991, Russian Federation.

The condensation of primary amines with N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamides was explored. Thus, a previously unknown recyclization of the starting material was observed in acidic ethanol in the presence of an amine, which provided the corresponding dihydropyrrolone derivative as the major reaction product. Based on this transformation, a practical and convenient one-pot synthetic method for substituted pyrrolo[3,4-b]pyridin-5-ones could be devised.

Melekhina V.G. , Komogortsev A.N. , Lichitsky B.V. , Mityanov V.S. , Fakhrutdinov A.N. , Dudinov A.A. , Migulin V.A. , Nelyubina Y.V. , Melnikova E.K. , Krayushkin M.M.
One-pot synthesis of substituted pyrrolo[3,4-b]pyridine-4,5-diones based on the reaction of N-(1-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines
Beilstein Journal of Organic Chemistry. 2019. V.15. P.2840-2846. DOI: 10.3762/bjoc.15.277 WOS Scopus OpenAlex

Web of science:	WOS:000500237000001
Scopus:	2-s2.0-85076021614
OpenAlex:	W2991599413

DB	Citing
OpenAlex	6
Scopus	3
Web of science	5