Home / Publications / 2-Methyl-11-nitro-5,6-dihydro-2H-2,6-methano- 1,3,5-benzoxadiazocin-4(3H)-one: Synthesis, Crystal Structure and Tautomerism in Dipolar Aprotic Solvents

2-Methyl-11-nitro-5,6-dihydro-2H-2,6-methano- 1,3,5-benzoxadiazocin-4(3H)-one: Synthesis, Crystal Structure and Tautomerism in Dipolar Aprotic Solvents

Valentina Fedorovna Sedova 1
Valentina Fedorovna Sedova
, 
Victor Petrovich Krivopalov 1
Victor Petrovich Krivopalov
, 
Yuriy Vasil'evich Gatilov 1
Yuriy Vasil'evich Gatilov
, 
Oleg Pavlovich Shkurko 1
Oleg Pavlovich Shkurko
10.1016/j.mencom.2013.05.020
Published 2013-05-08
Communication , Volume 23, Issue 3, 176-178
7
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Sedova V. F. et al. 2-Methyl-11-nitro-5,6-dihydro-2H-2,6-methano- 1,3,5-benzoxadiazocin-4(3H)-one: Synthesis, Crystal Structure and Tautomerism in Dipolar Aprotic Solvents // Mendeleev Communications. 2013. Vol. 23. No. 3. pp. 176-178.
GOST all authors (up to 50) Copy
Sedova V. F., Krivopalov V. P., Gatilov Y. V., Shkurko O. P. 2-Methyl-11-nitro-5,6-dihydro-2H-2,6-methano- 1,3,5-benzoxadiazocin-4(3H)-one: Synthesis, Crystal Structure and Tautomerism in Dipolar Aprotic Solvents // Mendeleev Communications. 2013. Vol. 23. No. 3. pp. 176-178.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2013.05.020
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.05.020
TI - 2-Methyl-11-nitro-5,6-dihydro-2H-2,6-methano- 1,3,5-benzoxadiazocin-4(3H)-one: Synthesis, Crystal Structure and Tautomerism in Dipolar Aprotic Solvents
T2 - Mendeleev Communications
AU - Sedova, Valentina Fedorovna
AU - Krivopalov, Victor Petrovich
AU - Gatilov, Yuriy Vasil'evich
AU - Shkurko, Oleg Pavlovich
PY - 2013
DA - 2013/05/08
PB - Mendeleev Communications
SP - 176-178
IS - 3
VL - 23
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2013_Sedova,
author = {Valentina Fedorovna Sedova and Victor Petrovich Krivopalov and Yuriy Vasil'evich Gatilov and Oleg Pavlovich Shkurko},
title = {2-Methyl-11-nitro-5,6-dihydro-2H-2,6-methano- 1,3,5-benzoxadiazocin-4(3H)-one: Synthesis, Crystal Structure and Tautomerism in Dipolar Aprotic Solvents},
journal = {Mendeleev Communications},
year = {2013},
volume = {23},
publisher = {Mendeleev Communications},
month = {May},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.05.020},
number = {3},
pages = {176--178},
doi = {10.1016/j.mencom.2013.05.020}
}
MLA
Cite this
MLA Copy
Sedova, Valentina Fedorovna, et al. “2-Methyl-11-nitro-5,6-dihydro-2H-2,6-methano- 1,3,5-benzoxadiazocin-4(3H)-one: Synthesis, Crystal Structure and Tautomerism in Dipolar Aprotic Solvents.” Mendeleev Communications, vol. 23, no. 3, May. 2013, pp. 176-178. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.05.020.

Abstract

Condensation of salicylaldehyde with nitroacetone and urea yields one diastereomer of the title compound. In DMF or DMSO solutions, this compound undergoes oxadiazocine ring opening leading to the equilibrium between its 2R*,6S*,11S*- and 2R*,6S*,11R*-diastereomers and 4-(2-hydroxyphenyl)-6-methyl-5-nitro-3,4-dihydropyrimidin-2(1H)-one.

References

1.
C. O. Kappe, Eur. J. Med. Chem., 2000, 35, 1043.
2.
Dihydropyrimidinones—a new class of anti-Staphylococcal antibiotics
Brands M., Endermann R., Gahlmann R., Krüger J., Raddatz S.
Bioorganic and Medicinal Chemistry Letters, 2003
3.
H. Prokopcova, D. Dallinger, G. Uray, H.Y. K. Kaan, V. Ulaganathan, F. Kozielski, C. Laggner and C. O. Kappe, ChemMedChem, 2010, 5, 1760.
6.
J. J. Baldwin, S.M. Pitzenberger and D. E. McClure, US Patent 4675321, 1987 (Chem. Abstr., 1987, 107, 242619).
7.
K. Atwal, US Patent 4684655, 1987 (Chem. Abstr., 1987, 107, 176066).
8.
Effect of tetrahydropyrimidine derivatives on the cardiovascular system
Vitolinya R.O., Kimenis A.A.
Pharmaceutical Chemistry Journal, 1989
9.
G. C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O’Reilly, J. Schwartz and M. F. Malley, J. Med. Chem. Lett., 1992, 35, 3254.
11.
An Efficacious Protocol for 4-Substituted 3,4-Dihydropyrimidinones: Synthesis and Calcium Channel Binding Studies
Singh K., Arora D., Falkowski D., Liu Q., Moreland R.S.
European Journal of Organic Chemistry, 2009
13.
Synthesis and study of the pharmacologic properties of derivatives of 1,2,3,4-tetrahydro-5-nitropyrimidine
Remennikov G.Y., Shavaran S.S., Boldyrev I.V., Kurilenko L.K., Klebanov B.M., Kukhar' V.P.
Pharmaceutical Chemistry Journal, 1991
14.
G. Ya. Remennikov, S.S. Shavaran, I.V. Boldyrev, N.A. Kapran, L.K. Kurilenko, V.G. Shevchuk and B. M. Klebanov, Pharm. Chem. J., 1994, 28, 322 (Khim. -Farm. Zh., 1994, 28, 25).
15.
Nitrodihydropyrimidines (review)
Remennikov G.Y.
Chemistry of Heterocyclic Compounds, 1997
16.
New potential of the classical Biginelli reaction
Vdovina S.V., Mamedov V.A.
Russian Chemical Reviews, 2008
17.
J. Svetlik, V. Hanus and J. Bella, J. Chem. Res. (S), 1991, 1, 4;.
18.
N.-Y. Fu, Y.-F. Yuan, Z. Cao, S.-W. Wang, J.-T. Wang and C. Peppe, . Tetrahedron, 2002, 58, 4801.
20.
E. M. H. Abbas, S.M. Abdallah, M.H. Abdoh, H.A. Tawfik and W. S. El-Hamouly, Turk. J. Chem., 2008, 32, 297.
21.
Bicyclic compounds obtained by the Biginelli reaction
Kurbanova M.M.
Russian Journal of Organic Chemistry, 2010
22.
Dibromination of 5-pyrazolones and 5-hydroxypyrazoles via dibromoisocyanuric acid
Cheng K., Wu J.B., Lin H., Huang J., Huang Y., Lin S., Lin T., Wong F.F.
Journal of Heterocyclic Chemistry, 2010
23.
Carbon 13 NMR Spectroscopy
Kalinowski H.-., Berger S., Braun S., Griffiths L.
Analytica Chimica Acta, 1989