GB1246312A - 4,5-substituted n-oxy and hydroxy hydroimidazoles - Google Patents
4,5-substituted n-oxy and hydroxy hydroimidazolesInfo
- Publication number
- GB1246312A GB1246312A GB4809368A GB4809368A GB1246312A GB 1246312 A GB1246312 A GB 1246312A GB 4809368 A GB4809368 A GB 4809368A GB 4809368 A GB4809368 A GB 4809368A GB 1246312 A GB1246312 A GB 1246312A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- formula
- hydrogen
- hydroxylamine
- organic group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
Abstract
1,246,312. N-Oxy and hydroxy-hydroimidazoles. SYNTEX ENERGY RESEARCH Inc., and VARIAN ENERGY. 10 Oct., 1968 [10 Jan., 1968; 26 June, 1968], No. 48093/68. Heading C2C. Novel di- and tetra-hydromidazoles having tertiary carbon atoms in the 4- and 5-positions, each tertiary carbon being bonded to three other carbon atoms, the carbon atom in the 2-position carrying a hydrogen atom and a further hydrogen atom or an organic group attached by means of a carbon atom forming part of the organic group in the case of the tetrahydroimidazoles, or carrying a hydrogen atom or an organic group attached by means of a carbon atom forming part of the organic group in the case of the dihydroimidazoles, and having at least one oxygen-bearing nitrogen atom in the imidazole ring, the nitrogen and oxygen together having one of the structures are prepared by condensing a bis-hydroxylamine, in which the hydroxylamine groups are attached to adjacent tertiary carbon atoms, with an aldehyde, or a functional derivative thereof, an orthoformate or a carbonate to obtain imidazoles containing the partial ring structure and, if required, oxidizing this product to form the alternative nitrogen and oxygen structures. Preferred imidazoles have the Formulµ I, II, III, IV and V in which X is an anion, R<SP>5</SP> is hydrogen or an organic group attached by means of a carbon atom and K<SP>1-4</SP> are each C 1-12 alkyl, alkenyl, alkynyl or aryl groups or R<SP>1</SP> and R<SP>2</SP> and/or R<SP>3</SP> and R<SP>4</SP> together represent C 3-10 alkylene or alkenylene groups. Preferred co-reactants of the bis-hydroxylamines include aldehydes R<SP>5</SP>CHO where R<SP>5</SP> is an alkyl, aryl or heterocyclic radical optionally substituted by other groups, including a further aldehydic group, whereby bis-hydroimidazoles are obtained, compounds R<SP>5</SP>CHXX<SP>1</SP> where X and X<SP>1</SP>, which are eliminated in the condensation, are halogen, -OR<SP>1</SP>, -NR<SP>1</SP> 2 or -SR<SP>1</SP> (R<SP>1</SP> being hydrogen or an aryl or alkyl group), compounds R<SP>5</SP>COX where X is halogen or other replaceable group and R<SP>5</SP> is an electron-withdrawing group, e.g. a haloalkyl or carbonyl group, or orthoesters R<SP>5</SP>CXX<SP>1</SP>X<SP>11</SP> where X is halogen, -OR<SP>1</SP>, -NR<SP>2</SP> 1 or -SR<SP>1</SP>. The group R<SP>5</SP> may be modified after ring formation, e.g. conversion of a chloromethyl group to an iodomethyl group or replacement of organic values of R<SP>5</SP>, e.g. alkoxycarbonyl or hydroxymethyl, by hydrogen. Oxidizing agents for converting the N,N<SP>1</SP> - dihydroxytetrahydroimidazoles ' to other N-O forms are selected in accordance with the required product, e.g. lead dioxide yields, depending on conditions, the dihydroimidazoles of the Formula (III) or the free radicals of the Formula (I), the latter being reduced to the former by treatment with metallic sodium or to the imidazoles of the Formula (IV) by refluxing in ethanolic HC1, the second reduction being reversed by H 2 O 2 oxidation. The free radicals I can be further oxidized, e.g. with chlorine, SO 2 Cl 2 or CF 3 COOH, to the ionic form of the Formula (V), strong oxidants which are readily reduced to the free radical. Oxidation of the dihydroxy form of the Formula (II) may be effected simultaneously with the ring-forming condensation. The preparation of a variety of 4,4,5,5-tetra-methylhydroimidazoles from the preferred hydroxylamine reactant, 2,3-dihydroxylamino-2,3. dimethylbutane. 2,3 -Dihydrozylamino-2,3-dimethylbutane is prepared by treating 2-nitropropane with bromine to obtain 2,3-dinitro- 2,3-dimethylbutane which is subsequently reduced with Zn to the hydroxylamine.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US69671868A | 1968-01-10 | 1968-01-10 | |
US74005568A | 1968-06-26 | 1968-06-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1246312A true GB1246312A (en) | 1971-09-15 |
Family
ID=27105854
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4809368A Expired GB1246312A (en) | 1968-01-10 | 1968-10-10 | 4,5-substituted n-oxy and hydroxy hydroimidazoles |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPS4936236B1 (en) |
BE (1) | BE724435A (en) |
DE (1) | DE1815788A1 (en) |
FR (1) | FR1592709A (en) |
GB (1) | GB1246312A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MTP837B (en) * | 1977-11-07 | 1979-10-22 | Hoffman La Roche And Co Aktien | Derivatives 2 finino-imidazolidire |
JPS6053362U (en) * | 1983-09-20 | 1985-04-15 | トキコ株式会社 | industrial robot |
US5849929A (en) * | 1997-09-26 | 1998-12-15 | Uniroyal Chemical Company, Inc. | Process for the preparation of imidazoline nitroxyl |
-
1968
- 1968-10-10 GB GB4809368A patent/GB1246312A/en not_active Expired
- 1968-11-08 JP JP8134068A patent/JPS4936236B1/ja active Pending
- 1968-11-21 FR FR1592709D patent/FR1592709A/fr not_active Expired
- 1968-11-25 BE BE724435D patent/BE724435A/xx unknown
- 1968-12-19 DE DE19681815788 patent/DE1815788A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
DE1815788A1 (en) | 1969-09-18 |
JPS4936236B1 (en) | 1974-09-28 |
FR1592709A (en) | 1970-05-19 |
BE724435A (en) | 1969-05-02 |
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