Synthesis and reduction of 6-nitroso-5,7-dimethyl-4,7 dihydro[1,2,4]triazolo[1,5-a]pyrimidine

Keywords: 4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidines, nitrosation, reduction, deuterium exchange, functionalization

Abstract

Nitrosation of 5,7-dimethyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine leads, with a moderate yield, to the formation of 6-nitrososubstituted derivative, a promising compound for the synthesis of low-molecular building blocks, based on 6-amino-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine. When 6-nitrosoderivative reacts with NaBH4, the reduction of dihydropyrimidine cycle takes place, while as NO-group remains unaffected, however, the reduction product exists as the oxime of 6-keto-5,7-dimethyl-4,5,6,7-tetrahydro[1,2,4]triazolo[1,5-a]pyrimidine, which chemical structure was unambiguously proved by deuterium exchange experiment in 1H NMR spectra.

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References

K. A. Ali, M. A. Elsayed, H. S. Abdalghfar // ARKIVOC. – 2011. – Р. 103–114.

Y. N. Mabkhot, A. M. Al-Majid, A. Barakat, S. Alshahrani, Y. Siddiqui // Molecules. – 2011. – Vol. 16. – P. 6502–6511.

U. Battaglia, C. J. Moody // J. Nat. Prod. – 2010. – Vol. 73. – P. 1938–1939.

4. M. A. Kolosov, E. H. Shvets, D. A. Manuenkov, S. A. Vlasenko, I. V. Omelchenko, S. V. Shishkina, V. D. Orlov. // Tetrahedron Lett. – 2017. – Vol. 58. – P. 1207–1210.

M. A. Kolosov, O. G. Kulyk, O. I. Starchenko, V. D. Orlov // Chem. Heterocycl. Compd. – 2013. – Vol. 49. – P. 1166–1171.

M. A. Kolosov, M. J. K. Al-Ogaili, O. G. Kulyk, V. D. Orlov // Chem. Heterocycl. Compd. – 2015. – Vol. 51. – P. 691–694.

Azageterotsikly na osnove α,β-nepredel’nykh ketonov / S. M. Desenko, V. D. Orlov. – Kharkov: Folio, 1998. – 148 p.

V. A. Chebanov, E. A. Muravyova, S. M. Desenko, V. I. Musatov, I. V. Knyazeva, S. V. Shishkina, O. V. Shishkin, C. O. Kappе // J. Comb. Chem. – 2006. – Vol. 8. – Р. 427–434.

V. M. Chernyshev, A. N. Sokolov, D. A. Khoroshkin, V. A. Taranushich // Russ. J. Org. Chem. – 2008. – Vol. 44. – Р. 715−722.

Published
2017-06-26
Cited
How to Cite
Kolosov, M. A., Shvets, O. G., & Orlov, V. D. (2017). Synthesis and reduction of 6-nitroso-5,7-dimethyl-4,7 dihydro[1,2,4]triazolo[1,5-a]pyrimidine. Kharkiv University Bulletin. Chemical Series, (28), 44-47. https://doi.org/10.26565/2220-637X-2017-28-06

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