THE USE OF 4-(BROMOMETHYLENE)-5,5-DIMETHYL-1,3-DIOXOLAN-2-ONE AS "MASKED" α-BROMO-α'-HYDROXY KETONE IN THE SYNTHESIS OF HETEROCYCLIC SYSTEMS

Authors

  • A. A. Bogolyubov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991
  • N. B. Chernysheva N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991
  • V. V. Semenov N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 119991

Keywords:

4-bromo-4-(bromomethyl)-5,5-dimethyl-1,3-dioxolan-2-one, 11a-hydroxy-1,1-dimethyl-3-oxo-1,5,11,11a-tetrahydro[1,3]oxazolo[3,4-a]pyrido[1,2-d]-10-pyrazinium bromide, 4-(bromomethylene)-5,5-dimethyl-1,3-dioxolan-2-one, 10b-(bromomethyl)-8,9-dimethoxy-1,1-dimethyl-1,5,6,10b-tetrahydro[1,3]oxazolo[4,3-a]isoquinolin-3-one, 2-imidazo[1,2-a]pyridin-2-yl-2-propanol, intramolecular amidoalkylation

Abstract

4-(Bromomethylene)-5,5-dimethyl-1,3-dioxolan-2-one was obtained on the basis of the readily obtainable 4-methylene-5,5-dimethyl-1,3-dioxolan-2-one. It forms 2-imidazo[1,2-a]pyridin-2-yl-2-propanol with 2-aminopyridine, 11a-hydroxy-1,1-dimethyl-3-oxo-1,5,11,11a-tetrahydro[1,3]oxazolo-[3,4-a]pyrido[1,2-d]-10-pyrazinium bromide with 2-(aminomethyl)pyridine, and the corresponding derivative of 4-hydroxyoxazolidin-2-one with 2-(3,4-dimethoxyphenyl)ethylamine. The last product was converted by intramolecular amidoalkylation without isolation into 10b-(bromomethyl)-8,9-dimethoxy-1,1-dimethyl-1,5,6,10b-tetrahydro[1,3]oxazolo[3,4-a]isoquinolin-3-one.

How to Cite
Bogolyubov, A. A.; Chernysheva, N. B.; Semenov, V. V. Chem. Heterocycl. Compd. 2004, 40, 1124. [Khim. Geterotsikl. Soedin. 2004, 1303.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000048283.51485.4e

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Published

2004-09-25

Issue

No. 9 (2004)

Section

Original Papers