GB867930A - Substituted pyridones - Google Patents

Substituted pyridones

Info

Publication number
GB867930A
GB867930A GB29481/59A GB2948159A GB867930A GB 867930 A GB867930 A GB 867930A GB 29481/59 A GB29481/59 A GB 29481/59A GB 2948159 A GB2948159 A GB 2948159A GB 867930 A GB867930 A GB 867930A
Authority
GB
United Kingdom
Prior art keywords
pyridone
alkyl
substituted
hydrogen
heating
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
GB29481/59A
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.)
US Filter Wallace and Tiernan Inc
Original Assignee
Wallace and Tiernan Inc
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 Wallace and Tiernan Inc filed Critical Wallace and Tiernan Inc
Publication of GB867930A publication Critical patent/GB867930A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)

Abstract

The invention comprises compounds of the formula: <FORM:0867930/IV (b)/1> (wherein R1 is hydroxy, alkoxy, amino or alkylamino; R2 is hydrogen, alkyl or alkanoyl and R3 is hydrogen or alkyl, each alkyl radical in these groups containing at most 8 carbon atoms) and non-toxic acid-addition salts thereof. They may be prepared by reaction of methyl coumalate with the appropriately substituted aniline or phenylene diamine, which frequently leads to an intermediate of the formula: <FORM:0867930/IV (b)/2> which is then cyclized to the required pyridone by heating in basic solution e.g. aqueous sodium carbonate. The product may be either the methyl ester of the 1-substituted-5-carboxy-2-pyridone or, if heating is prolonged, the free acid. Either product can, if required, be converted to other esters, amides or substituted amides by common procedures. The amino group in the pyridone products can also, if required, be subjected to further changes such as alkylation or arylation or, conversely, acyl groups can be removed. Examples are given, and a hydrochloride and picrate salt are described.
GB29481/59A 1958-11-12 1959-08-28 Substituted pyridones Expired GB867930A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US867930XA 1958-11-12 1958-11-12

Publications (1)

Publication Number Publication Date
GB867930A true GB867930A (en) 1961-05-10

Family

ID=22200951

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29481/59A Expired GB867930A (en) 1958-11-12 1959-08-28 Substituted pyridones

Country Status (1)

Country Link
GB (1) GB867930A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0268964A1 (en) * 1986-11-27 1988-06-01 Bayer Ag Process for the preparation of 6-hydroxy-3-pyridine-carboxylic-acid esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0268964A1 (en) * 1986-11-27 1988-06-01 Bayer Ag Process for the preparation of 6-hydroxy-3-pyridine-carboxylic-acid esters
US4849519A (en) * 1986-11-27 1989-07-18 Bayer Aktiengesellschaft Preparation of 6-hydroxy-3-pyridinecarboxylic acid esters

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