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THE SYNTHESIS OF SOME SULFONAMIDES BASED ON 2,3-DIHYDRO-1H-PYRROLO[3,4-c]PYRIDINE

Martins Ikaunieks, Fredrik Björkling, Einars Loza
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Abstract


Synthetic protocols for the preparation of 1-oxo-, 3-oxo-, and 1,3-dioxopyrrolo[3,4-c]pyridines which contain sulfonamide groups linked to the pyrrole nitrogen atom of the pyrrolo[3,4-c]pyridine cycle by a flexible (CH2)6 aliphatic linker were developed. 1,3-Dioxopyrrolo[3,4-c]pyridines were obtained from 3,4-pyridinedicarboxylic acid by condensation of intermediate methyl 3-(chlorocarbonyl)isonicotinate with amines. 3-Oxopyrrolo[3,4-c]pyridines were prepared by regioselective reduction of 1,3-dioxopyrrolo[3,4-c]pyridines with a tin dust followed by treatment with triethylsilane. 1-Oxopyrrolo[3,4-c]pyridines were prepared by a synthetic sequence consisting of the treatment of methyl isonicotinate with N-bromosuccinimide and the following condensation of the obtained ethyl 3-bromomethylisonicotinate with primary amines.

How to Cite
Ikaunieks, M.; Björkling, F.; Loza, E. Chem. Heterocycl. Compd. 2015, 51, 658. [Khim. Geterotsikl. Soedin. 2015, 51, 658.]

For this article in the English edition see DOI 10.1007/s10593-015-1753-y


Keywords


2,3-dihydro-1H-pyrrolo[3,4-c]pyridine; pyridine; sulfonamide; cyclization; reduction

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