Home / Publications / Chlorination of 5-nitro-6-methyluracil and its N(1),N(3)-dimethyl analogue with molecular chlorine

Chlorination of 5-nitro-6-methyluracil and its N(1),N(3)-dimethyl analogue with molecular chlorine

Inna Borisovna Chernikova 1
Inna Borisovna Chernikova
, 
Sergei Leonidovich Khursan 1
Sergei Leonidovich Khursan
, 
Marat Sabirovich Yunusov 1
Marat Sabirovich Yunusov
, 
Rustam A Yumagulov 1, 2
Rustam A Yumagulov
10.1016/j.mencom.2015.05.022
Published 2015-04-28
Communication , Volume 25, Issue 3, 221-223
5
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Chernikova I. B. et al. Chlorination of 5-nitro-6-methyluracil and its N(1),N(3)-dimethyl analogue with molecular chlorine // Mendeleev Communications. 2015. Vol. 25. No. 3. pp. 221-223.
GOST all authors (up to 50) Copy
Chernikova I. B., Khursan S. L., Yunusov M. S., Yumagulov R. A. Chlorination of 5-nitro-6-methyluracil and its N(1),N(3)-dimethyl analogue with molecular chlorine // Mendeleev Communications. 2015. Vol. 25. No. 3. pp. 221-223.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2015.05.022
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.05.022
TI - Chlorination of 5-nitro-6-methyluracil and its N(1),N(3)-dimethyl analogue with molecular chlorine
T2 - Mendeleev Communications
AU - Chernikova, Inna Borisovna
AU - Khursan, Sergei Leonidovich
AU - Yunusov, Marat Sabirovich
AU - Yumagulov, Rustam A
PY - 2015
DA - 2015/04/28
PB - Mendeleev Communications
SP - 221-223
IS - 3
VL - 25
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2015_Chernikova,
author = {Inna Borisovna Chernikova and Sergei Leonidovich Khursan and Marat Sabirovich Yunusov and Rustam A Yumagulov},
title = {Chlorination of 5-nitro-6-methyluracil and its N(1),N(3)-dimethyl analogue with molecular chlorine},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.05.022},
number = {3},
pages = {221--223},
doi = {10.1016/j.mencom.2015.05.022}
}
MLA
Cite this
MLA Copy
Chernikova, Inna Borisovna, et al. “Chlorination of 5-nitro-6-methyluracil and its N(1),N(3)-dimethyl analogue with molecular chlorine.” Mendeleev Communications, vol. 25, no. 3, Apr. 2015, pp. 221-223. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.05.022.

Abstract

The chlorination of 6-methyl-5-nitrouracil with chlorine in methanol results in a two-component mixture of 5-chloro-6-methyl-6-methoxy-5-nitro-5,6-dihydrouracils, while the chlorination of 5-nitro-1,3,6-trimethyluracil under similar conditions gives a mixture of 5-chloro-6-hydroxy-5-nitro-1,3,6-trimethyl-5,6-dihydrouracils. The structures of the chlorination products were suggested based on quantum-chemical calculations

References

1.
10.1016/j.mencom.2015.05.022_bib0005
Ovchinnikov Yu.
Bioorganicheskaya khimiya (Bioorganic Chemistry), 1987
2.
Synthesis and Antiviral Activity of 1-{[2-(Phenoxy)ethoxy]methyl}uracil Derivatives
Novikov M.S., Ozerov A.A., Orlova Y.A., Buckheit R.W.
Chemistry of Heterocyclic Compounds, 2005
3.
Synthesis of acyclic analogs of pyrimidine nucleosides with aromatic units in the side chain
Novikov M.S., Ozerov A.A., Brel' A.K., Solodunova G.N., Ozerova T.P.
Chemistry of Heterocyclic Compounds, 1996
4.
Synthesis and antiviral activity of new unsaturated pyrimidine acyclonucleosides
Ozerov A.A., Novikov M.S., Brel' A.K., Andreeva O.T., Vladykov G.V., Boreko E.I., Korobchenko L.V., Vervetchenko S.G.
Pharmaceutical Chemistry Journal, 1991
5.
Structure and activity relationships of novel uracil derivatives as topical anti-inflammatory agents
Isobe Y., Tobe M., Inoue Y., Isobe M., Tsuchiya M., Hayashi H.
Bioorganic and Medicinal Chemistry, 2003
6.
10.1016/j.mencom.2015.05.022_bib0030
Lazareva
Med. Vestn. Bashkortostana, 2007
7.
V. A. Myshkin and A. B. Bakirov, Oksimetiluratsil. Ocherki eksperimental’noi farmakologii (Oxymethyluracil. Essays of Experimental Pharmacology), DAR, Ufa, 2001, p. 218 (in Russian).
8.
10.1016/j.mencom.2015.05.022_bib0040
Gimadieva
Bash. Khim. Zh., 2007
9.
Synthesis and characterization of 5-bromo-3-sec-butyl-6-methyluracil
Ren H., Yang Y., Lin J., Qi Y., Zhang Y.
Frontiers of Chemistry in China, 2008
10.
Oxidative halogenation of 6-methyluracil
Kasradze V.G., Ignatyeva I.B., Khusnutdinov R.A., Suponitskii K.Y., Antipin M.Y., Yunusov M.S.
Chemistry of Heterocyclic Compounds, 2012
11.
Electrophilic ipso-substitution in uracil derivatives
Chernikova I.B., Khursan S.L., Spirikhin L.V., Yunusov M.S.
Russian Chemical Bulletin, 2013
12.
10.1016/j.mencom.2015.05.022_bib0060
Fattakhov Kh.
PhD Thesis, Ufa, 2011
14.
J. Mathieu and R. Panico, Kurs teoreticheskikh osnov organicheskoi khimii (Course of Theoretical Bases of Organic Chemistry), Mir, Moscow, 1975, p. 80 (in Russian).
15.
10.1016/j.mencom.2015.05.022_bib0075
Frisch
Gaussian 09, Revision C.1, Gaussian, Inc., Wallingford CT, 2009
16.
G. A. Zhurko, ChemCraft, Version 1.6, http://www.chemcraftprog.com.
20.
Self‐consistent molecular orbital methods. XX. A basis set for correlated wave functions
Krishnan R., Binkley J.S., Seeger R., Pople J.A.
Journal of Chemical Physics, 1980
21.
Quantum Mechanical Continuum Solvation Models
Tomasi J., Mennucci B., Cammi R.
Chemical Reviews, 2005
22.
Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
Reed A.E., Curtiss L.A., Weinhold F.
Chemical Reviews, 1988
23.
E. Kirby, Anomernyi effekt kislorodsoderzhashchikh soedinenii (Anomeric Effect of Oxygen-containing Compounds), Mir, Moscow, 1985, p. 171 (in Russian).