GB602025A - Improvements in and relating to the production of pseudoxazolone derivatives and reduction products thereof - Google Patents
Improvements in and relating to the production of pseudoxazolone derivatives and reduction products thereofInfo
- Publication number
- GB602025A GB602025A GB1094144A GB1094144A GB602025A GB 602025 A GB602025 A GB 602025A GB 1094144 A GB1094144 A GB 1094144A GB 1094144 A GB1094144 A GB 1094144A GB 602025 A GB602025 A GB 602025A
- Authority
- GB
- United Kingdom
- Prior art keywords
- treated
- pyridine
- acetic anhydride
- pseudoxazolone
- derivatives
- 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/36—One oxygen atom
- C07D263/42—One oxygen atom attached in position 5
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Pseudoxazolone derivatives of the general formula <FORM:0602025/IV(b)/1> where R is hydrogen or a hydrocarbon group are prepared by subjecting a -halogenoacylamino acids of the general formula CO2H.CHR-NH-COCH (hal) R1 to treatment with a tertiary nitrogen base or a strong inorganic base and a dehydrating agent. An essential condition for the success of the process is that the group R.CH= is of such a character that the formation of the unsaturated group (R minus H)=C= cannot occur in the removal of H.Hal, such as where R is H or phenyl. The compounds so produced may be hydrogenated to oxazolones. In examples: (1) a -bromophenacetylglycine is treated with acetic anhydride and pyridine; (2) a -bromphenacetylalanine is similarly treated; (3) a -bromphenacetylalanine is mixed with pyridine, the separated pyridinium bromide treated with more pyridine and acetic anhydride; (4) as in (2) but using an N-sodium hydroxide solution of a -bromophenacetylalanine; (5) phenacetylalanine is heated with acetic anhydride and then treated with pyridine and bromine; (6) mandelylaline, made by condensation of alanine with acetylmandelyl chloride, is treated as in examples (1)-(4) above; (7) 4-methyl-2-benzylidenepseudoxazolone is hydrogenated in ethyl acetate solution in presence of a Raney nickel catalyst to form 4-methyl-2-benzyl-oxazolone.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1094144A GB602025A (en) | 1944-06-07 | 1944-06-07 | Improvements in and relating to the production of pseudoxazolone derivatives and reduction products thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1094144A GB602025A (en) | 1944-06-07 | 1944-06-07 | Improvements in and relating to the production of pseudoxazolone derivatives and reduction products thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
GB602025A true GB602025A (en) | 1948-05-19 |
Family
ID=9977116
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1094144A Expired GB602025A (en) | 1944-06-07 | 1944-06-07 | Improvements in and relating to the production of pseudoxazolone derivatives and reduction products thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB602025A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4727155A (en) * | 1985-09-04 | 1988-02-23 | American Cyanamid Company | Oxazolinone compounds useful as intermediates for the preparation of insecticidal and acaricidal agents |
-
1944
- 1944-06-07 GB GB1094144A patent/GB602025A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4727155A (en) * | 1985-09-04 | 1988-02-23 | American Cyanamid Company | Oxazolinone compounds useful as intermediates for the preparation of insecticidal and acaricidal agents |
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