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-2 H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines

Valeriya G Melekhina; Andrey N Komogortsev; Boris V Lichitsky; Vitaly S Mityanov; Artem N Fakhrutdinov; Arkady A Dudinov; Vasily A Migulin; Yulia V Nelyubina; Elizaveta K Melnikova; Michail M Krayushkin

doi:10.3762/bjoc.15.277

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-2 H-pyran-3-yl)-2-oxo-2-arylethyl)acetamide with amines

Beilstein J Org Chem. 2019 Nov 25:15:2840-2846. doi: 10.3762/bjoc.15.277. eCollection 2019.

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.

Abstract

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.

Keywords: condensation; dihydropyrrolone derivative; one-pot synthesis; pyrrolo[3,4-b]pyridine-4,5-diones; recyclization.