MD4150C1 - Process for producing coordinative compounds of Co(II), Ni(II) and Zn(II) with 2-nitro-4,5-diphenylimidazole starting from 4,5-diphenylimidazole and nitrates of said metals - Google Patents
Process for producing coordinative compounds of Co(II), Ni(II) and Zn(II) with 2-nitro-4,5-diphenylimidazole starting from 4,5-diphenylimidazole and nitrates of said metalsInfo
- Publication number
- MD4150C1 MD4150C1 MDA20110087A MD20110087A MD4150C1 MD 4150 C1 MD4150 C1 MD 4150C1 MD A20110087 A MDA20110087 A MD A20110087A MD 20110087 A MD20110087 A MD 20110087A MD 4150 C1 MD4150 C1 MD 4150C1
- Authority
- MD
- Moldova
- Prior art keywords
- diphenylimidazole
- nitrates
- nitro
- compounds
- producing
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- CPHGOBGXZQKCKI-UHFFFAOYSA-N 4,5-diphenyl-1h-imidazole Chemical compound N1C=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CPHGOBGXZQKCKI-UHFFFAOYSA-N 0.000 title abstract 3
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 title abstract 3
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 title abstract 3
- STGHAEAHYGLKLG-UHFFFAOYSA-N 2-nitro-4,5-diphenyl-1h-imidazole Chemical compound N1C([N+](=O)[O-])=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 STGHAEAHYGLKLG-UHFFFAOYSA-N 0.000 title abstract 2
- 239000002184 metal Substances 0.000 title abstract 2
- 229910052751 metal Inorganic materials 0.000 title abstract 2
- 150000002739 metals Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 150000002823 nitrates Chemical class 0.000 title abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 150000002500 ions Chemical class 0.000 abstract 3
- 230000009920 chelation Effects 0.000 abstract 2
- 238000006396 nitration reaction Methods 0.000 abstract 2
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 229910001960 metal nitrate Inorganic materials 0.000 abstract 1
- 230000000802 nitrating effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000004957 nitroimidazoles Chemical class 0.000 abstract 1
- 239000013110 organic ligand Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Catalysts (AREA)
Abstract
The invention relates to the chemistry of coordinative compounds with organic ligands from the class of nitroimidazoles, which can be used as biologically active compounds, catalysts, etc.The invention consists in that it is proposed a process for producing coordinative compounds of some biometals, such as Co(II), Ni(II) and Zn(II) with 2-nitro-4,5-diphenylimidazole upon interaction of 4,5-diphenylimidazole with nitrates of Co(II), Ni(II) and Zn(II) in pure methanol or containing a small amount of water. In solvothermal conditions (170°C, 3 hours) the heterocyclic nucleus of 4,5-diphenylimidazole is nitrated in position C2, and the ions of initial metals are associated with the nitration product through chelation, with the involvement of the nitro group and one nitrogen atom of the heterocycle nucleus. At the same time the solvent (methanol) complements the coordination sphere of the central ion.The result of the invention consists in that in solvothermal conditions it is concomitantly produced the nitration of heterocyclic nucleus and the coordination of the reaction product, at the same time the metal nitrates serve as acid-free nitrating agents and a source of central ions for chelation with the final nitroimidazole.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20110087A MD4150C1 (en) | 2011-10-11 | 2011-10-11 | Process for producing coordinative compounds of Co(II), Ni(II) and Zn(II) with 2-nitro-4,5-diphenylimidazole starting from 4,5-diphenylimidazole and nitrates of said metals |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20110087A MD4150C1 (en) | 2011-10-11 | 2011-10-11 | Process for producing coordinative compounds of Co(II), Ni(II) and Zn(II) with 2-nitro-4,5-diphenylimidazole starting from 4,5-diphenylimidazole and nitrates of said metals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4150B1 MD4150B1 (en) | 2012-02-29 |
| MD4150C1 true MD4150C1 (en) | 2012-09-30 |
Family
ID=45815372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20110087A MD4150C1 (en) | 2011-10-11 | 2011-10-11 | Process for producing coordinative compounds of Co(II), Ni(II) and Zn(II) with 2-nitro-4,5-diphenylimidazole starting from 4,5-diphenylimidazole and nitrates of said metals |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4150C1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD4178C1 (en) * | 2012-02-27 | 2013-02-28 | Институт Химии Академии Наук Молдовы | Process for producing 2-nitro-4,5-diphenylimidazole |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199592A (en) * | 1978-08-29 | 1980-04-22 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-2-nitroimidazoles |
| US4241060A (en) * | 1977-08-19 | 1980-12-23 | Hoffmann-La Roche Inc. | Nitroimidazoles and compositions thereof |
| US5008398A (en) * | 1988-10-15 | 1991-04-16 | Basf Aktiengesellschaft | Preparation of p-nitrophenyl-imidazoles |
| EP0510036A1 (en) * | 1990-01-12 | 1992-10-28 | Rhone Poulenc Rorer Sa | 2-substituted 4,5-diphenyl-imidazoles. |
| WO1994019310A1 (en) * | 1993-02-26 | 1994-09-01 | Instituto Nacional De Engenharia E Tecnologia Industrial | New process for the nitration of aromatic compounds in mild, non-corrosive conditions |
| RU2021249C1 (en) * | 1990-10-16 | 1994-10-15 | Индивидуально-частное предприятие "Ост-Вест" | Method of synthesis of aromatic 1,2-diketones |
| CN1736976A (en) * | 2005-08-30 | 2006-02-22 | 南京大学 | Use of aluminum nitrate in aromatic ring nitration |
| WO2008070336A2 (en) * | 2006-10-27 | 2008-06-12 | Natural Pharmacia International, Inc. | Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof |
| US20100004460A1 (en) * | 2007-01-23 | 2010-01-07 | Pola Pharma Inc | Method for producing 2-nitroimidazole derivative |
-
2011
- 2011-10-11 MD MDA20110087A patent/MD4150C1/en not_active IP Right Cessation
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4241060A (en) * | 1977-08-19 | 1980-12-23 | Hoffmann-La Roche Inc. | Nitroimidazoles and compositions thereof |
| US4199592A (en) * | 1978-08-29 | 1980-04-22 | E. I. Du Pont De Nemours And Company | Antiinflammatory 4,5-diaryl-2-nitroimidazoles |
| US5008398A (en) * | 1988-10-15 | 1991-04-16 | Basf Aktiengesellschaft | Preparation of p-nitrophenyl-imidazoles |
| EP0510036A1 (en) * | 1990-01-12 | 1992-10-28 | Rhone Poulenc Rorer Sa | 2-substituted 4,5-diphenyl-imidazoles. |
| RU2021249C1 (en) * | 1990-10-16 | 1994-10-15 | Индивидуально-частное предприятие "Ост-Вест" | Method of synthesis of aromatic 1,2-diketones |
| WO1994019310A1 (en) * | 1993-02-26 | 1994-09-01 | Instituto Nacional De Engenharia E Tecnologia Industrial | New process for the nitration of aromatic compounds in mild, non-corrosive conditions |
| CN1736976A (en) * | 2005-08-30 | 2006-02-22 | 南京大学 | Use of aluminum nitrate in aromatic ring nitration |
| WO2008070336A2 (en) * | 2006-10-27 | 2008-06-12 | Natural Pharmacia International, Inc. | Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof |
| US7842278B2 (en) * | 2006-10-27 | 2010-11-30 | Natural Pharmacia International, Inc. | Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof |
| US20100004460A1 (en) * | 2007-01-23 | 2010-01-07 | Pola Pharma Inc | Method for producing 2-nitroimidazole derivative |
Non-Patent Citations (9)
| Title |
|---|
| Bergan T. Antibacterial activity and pharmacokinetics of nitroimidazoles. A review. Scand. J. Infect. Dis., 1985, vol. 17 (Suppl. 46), p. 64-71 * |
| Charlson R.H., Brown T.L. Inorg. Chem., vol. 5, no. 2, 1966, p. 268 * |
| Cornelius A., Laszlo P., "Clay supported copper(II) and iron(III) nitrates: novel multipurpose reagents for organic synthesis". Synthesis, October, p. 909-918 (1985) * |
| Es T. van and Backerberg O.G. Substitution of 4,5-diphenyl-oxazoles and some related compounds. J. Chem. Soc., 1963, p. 1363-1370 * |
| Palamaru M.N., Iordan A.R., Cecal A. Chimie bioanorganică şi metalele vieţii, BIT, Iaşi, 1997, 395 p. * |
| Sathururu R and Biehl Ed, "Facile, high-yield, regioselective synthesis of ortho-nitroderivatives of hydroxy heterocycles using cerium (IV) ammonium nitrate", ARCHIVOC, The Archive for Organic Chemistry, 2004 (xiv) 89-95. Published on the web 23 Sep 2004, (regăsit în Internet la 2011.12.20, url: http://quod.lib.umich.edu/cgi/p/pod/dod-idx?c=ark;idno=5550190.0005.e09 ) * |
| Yagovkin A.Yu. and Bakibaev A.A. Formation of a 2-Nitro Derivative in the Oxidation of 4,5-Diphenylimidazole to Benzyl using Nitric Acid. Chemistry of Heterocyclic Compounds, 1995, vol.31, No. 12, p. 1696-1697 * |
| Новиков С.С. и др. Химия Гетероциклических Соединений, 1970, № 4, с. 503 * |
| Эйхгорн Г. Неорганическая химия, Мир, Москва, 1978, том 1, том 2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4150B1 (en) | 2012-02-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |