DIOXOPYRROLINES .56. SYNTHESIS OF 2,3-DIALKOXY-1H-PYRROLE VIA REDUCTION OF DIOXOPYRROLINE WITH SODIUM HYDROSULFITE

Authors
SANO T SEKI M TODA J TSUDA Y
Citation
T. Sano et al., DIOXOPYRROLINES .56. SYNTHESIS OF 2,3-DIALKOXY-1H-PYRROLE VIA REDUCTION OF DIOXOPYRROLINE WITH SODIUM HYDROSULFITE, Heterocycles, 36(11), 1993, pp. 2541-2547
Citations number
3
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
36
Issue
11
Year of publication
1993
Pages
2541 - 2547
Database
ISI
SICI code
0385-5414(1993)36:11<2541:D.SO2V>2.0.ZU;2-7
Abstract
Reduction of IH-pyrrole-2,3-dione (3 and 7) with sodium hydrosulfite t ook place selectively in a 1,4-manner. Methylation of the product with diazomethane gave 1,5-dihydro-3-methoxy-2H-pyrrol-2-one (5 and 8) in good yield. Treatment of the methyl ether (5 or 8) with triethyloxoniu m tetrafluoroborate caused ethylation of the lactam carbonyl with conc omitant deprotonation to give 2,3-dialkoxy-1H-pyrrole (9). This conver sion provides a simple synthetic method of 2,3-dialkoxypyrroles.