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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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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REFERENCES

  1. P. Dimroth and H. Pasedach, Ger. Patent 1158079; Chem. Abstr., 38, 6849 (1964).

    Google Scholar 

  2. C. C. Browne and N. Punja, J. Chem. Soc., Perkin Trans. 1, 16, 1525 (1975).

    Google Scholar 

  3. R. Adams and J. S. Dis, J. Am. Chem. Soc., 80, 4618 (1958).

    Google Scholar 

  4. J. Fournier, C. Bruneau, and P. H. Dixneuf, Synlett, 5, 453 (1992).

    Google Scholar 

  5. A. A. Bogolyubov, N. B. Chernysheva, V. V. Nesterov, M. Yu. Antipin, and V. V. Semenov, Khim. Geterotsikl. Soedin., 1152 (2004).

  6. M. I. Collado, N. Sotomayor, M.-J. Villa, and E. Lette, Tetrahedron Lett., 37, 6193 (1996).

    Google Scholar 

  7. N. B. Chernysheva, A. A. Bogolyubov, V. V. Murav'ev, V. V. Elkin, and V. V. Semenov, Khim. Geterotsikl. Soedin., 1409 (2000).

  8. N. B. Chernysheva, A. A. Bogolyubov, and V. V. Semenov, Khim. Geterotsikl. Soedin., 241 (1999).

  9. V. Nuti and M. F. Saetone, Tetrahedron, 26, 3875 (1970).

    Google Scholar 

  10. P. Dimroth and H. Pasedach, Ger. Patent 1098953; Chem. Abstr., 56, 2453 (1962).

    Google Scholar 

  11. www.chemical-block.com.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Russia

    A. A. Bogolyubov, N. B. Chernysheva & V. V. Semenov

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  1. A. A. Bogolyubov
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  2. N. B. Chernysheva
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  3. V. V. Semenov
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Bogolyubov, A.A., Chernysheva, N.B. & Semenov, V.V. 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. Chemistry of Heterocyclic Compounds 40, 1124–1130 (2004). https://doi.org/10.1023/B:COHC.0000048283.51485.4e

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  • DOI: https://doi.org/10.1023/B:COHC.0000048283.51485.4e

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