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 thereof

Info

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
Application number
GB1094144A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ROBERT ROBINSON KT
STEPHEN GERALD WALEY
Original Assignee
ROBERT ROBINSON KT
STEPHEN GERALD WALEY
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by ROBERT ROBINSON KT, STEPHEN GERALD WALEY filed Critical ROBERT ROBINSON KT
Priority to GB1094144A priority Critical patent/GB602025A/en
Publication of GB602025A publication Critical patent/GB602025A/en
Expired legal-status Critical Current

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.
GB1094144A 1944-06-07 1944-06-07 Improvements in and relating to the production of pseudoxazolone derivatives and reduction products thereof Expired GB602025A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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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