GB920140A - Process for the production of new derivatives of hydrogenated pyridones - Google Patents
Process for the production of new derivatives of hydrogenated pyridonesInfo
- Publication number
- GB920140A GB920140A GB1890361A GB1890361A GB920140A GB 920140 A GB920140 A GB 920140A GB 1890361 A GB1890361 A GB 1890361A GB 1890361 A GB1890361 A GB 1890361A GB 920140 A GB920140 A GB 920140A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- radical
- ketones
- ch2cor3
- formula
- 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
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 title 1
- -1 hydrocarbon radicals Chemical class 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 239000000543 intermediate Substances 0.000 abstract 3
- 150000002576 ketones Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000002730 mercury Chemical class 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001241 acetals Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 abstract 1
- 150000002084 enol ethers Chemical class 0.000 abstract 1
- 125000005283 haloketone group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises compounds of the formula <FORM:0920140/IV(a)/1> (wherein R1 and R2 are hydrocarbon radicals or together represent an alkylene radical of 4 to 7 carbon atoms, R3 is an alkyl radical of at most 5 carbon atoms, an aryl or an aralkyl radical and R4 is an alkyl radical of at most 4 carbon atoms or an aryl radical) and their preparation by condensing, in presence of a mineral acid, an isoxazole of the formula <FORM:0920140/IV(a)/2> with a compound which yields a carbonium ion \sJC(R1.R2)CH2COR3. Such compounds may be, for example, unsaturated ketones C(R1.R2)=CHCOR3, hydroxy ketones HO.C (R1R2)CH2COR3 or haloketones Hal.C(R1.R2) CH2COR3 or ketals thereof or \sJC(R1R2) CH2CCR5 (R5 being hydrogen or an alkyl radical containing one less carbon atoms than the number of carbon atoms in R3 when this is alkyl, suitable compounds being the alcohols HO.C(R1.R2)CH2CCR5) prepared from ketones R1.R2CO and suitably substituted propargyl magnesium halides. Reaction with the unsaturated ketones may proceed through the intermediate <FORM:0920140/IV(a)/3> which compound, or an acetal, enol ether or enol ester thereof may then be cyclized to the required compound by treatment with an acid or basic condensing agent; or it may proceed through the intermediate <FORM:0920140/IV(a)/4> or through the 3,4-dihydro-derivatives of the required products, which may then be obtained by dehydration or dehydrogenation. Reaction with the unsaturated alcohols proceeds direct if a mercury salt is also present, or, if this is absent, intermediates of the formula <FORM:0920140/IV(a)/5> are obtained, and then converted into the required products by treatment with sulphuric acid containing a mercury salt. Detailed examples are provided.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH644360A CH416621A (en) | 1960-06-07 | 1960-06-07 | Process for the preparation of new derivatives of hydrogenated pyridones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB920140A true GB920140A (en) | 1963-03-06 |
Family
ID=4309708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1890361A Expired GB920140A (en) | 1960-06-07 | 1961-05-25 | Process for the production of new derivatives of hydrogenated pyridones |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE604658A (en) |
| CH (1) | CH416621A (en) |
| DK (1) | DK103076C (en) |
| ES (1) | ES268395A1 (en) |
| GB (1) | GB920140A (en) |
-
1960
- 1960-06-07 CH CH644360A patent/CH416621A/en unknown
-
1961
- 1961-05-25 GB GB1890361A patent/GB920140A/en not_active Expired
- 1961-06-06 DK DK336662A patent/DK103076C/en active
- 1961-06-06 BE BE604658A patent/BE604658A/en unknown
- 1961-06-20 ES ES0268395A patent/ES268395A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE604658A (en) | 1961-12-06 |
| DK103076C (en) | 1965-11-15 |
| ES268395A1 (en) | 1961-12-01 |
| CH416621A (en) | 1966-07-15 |
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