GB791719A - Improvements in or relating to the production of cyclic hydroxamic acids of the pyridine series - Google Patents

Improvements in or relating to the production of cyclic hydroxamic acids of the pyridine series

Info

Publication number
GB791719A
GB791719A GB4727/56A GB472756A GB791719A GB 791719 A GB791719 A GB 791719A GB 4727/56 A GB4727/56 A GB 4727/56A GB 472756 A GB472756 A GB 472756A GB 791719 A GB791719 A GB 791719A
Authority
GB
United Kingdom
Prior art keywords
formula
dimethoxy
carbon atoms
hydroxylamine
compounds
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
GB4727/56A
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.)
Sadolin and Holmblad AS
Original Assignee
Sadolin and Holmblad AS
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 Sadolin and Holmblad AS filed Critical Sadolin and Holmblad AS
Publication of GB791719A publication Critical patent/GB791719A/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
    • C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom

Abstract

The invention comprises compounds of the formula: <FORM:0791719/IV (b)/1> (wherein R and R1 are hydrogen or alkyl groups of 1 to 8 carbon atoms and R11 is a hydrocarbon group of 4 to 10 carbon atoms) and their preparation by reacting a compound of the formula: <FORM:0791719/IV (b)/2> (wherein the lower alkyl groups have from 1 to 8 carbon atoms) with a Grignard reagent R11Mg-(halogen) and treating the resulting compound of the formula: <FORM:0791719/IV (b)/3> with hydroxylamine or an acid addition salt thereof under hydrolysing conditions, the reaction with hydroxylamine or a salt thereof preferably being performed in methanol and the hydrolysis preferably being effected with ammonium hydroxide. In examples: (1) n-hexyl magnesium bromide and 2 : 5-dimethoxy-2 : 5-dihydrofuroic acid methyl ester give 2 : 5-dimethoxy - 2 - (a - oxo - n - heptyl) - 2:5 - dihydrofuran which on standing with hydroxylamine hydrochloride in methanol followed by hydrolysis with ammonium hydroxide gives 1:5 - dihydroxy - 6 - (n - hexyl) - 2 - pyridone: (2) the corresponding cyclohexyl compounds are similarly prepared. Reference is also made to the preparation of the corresponding n-butyl, n-amyl, n-octyl, n-decyl and n-phenyl compounds and to replacement of the 2 : 5-dimethoxy - 2:5 - dihydrofuroic acid methyl ester by a 3 and/or 4-(lower alkyl)-substituted derivative thereof, e.g. the 4-methyl, 3:4-dimethyl, 3-isopropyl and 3-tertiary butyl substituted derivatives; and to conversion of the 1 : 5 - dihydroxy - 2 - pyridones of the invention to the corresponding 5-hydroxy-2-piperidones of the formula: <FORM:0791719/IV (b)/4> by high pressure hydrogenation in the presence of Raney nickel.
GB4727/56A 1955-02-15 1956-02-15 Improvements in or relating to the production of cyclic hydroxamic acids of the pyridine series Expired GB791719A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US791719XA 1955-02-15 1955-02-15

Publications (1)

Publication Number Publication Date
GB791719A true GB791719A (en) 1958-03-12

Family

ID=22148876

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4727/56A Expired GB791719A (en) 1955-02-15 1956-02-15 Improvements in or relating to the production of cyclic hydroxamic acids of the pyridine series

Country Status (1)

Country Link
GB (1) GB791719A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0138420A2 (en) * 1983-09-23 1985-04-24 National Research Development Corporation Pharmaceutical compositions containing 1-hydroxypyrid-2-one derivatives
US4912118A (en) * 1983-09-23 1990-03-27 National Research Development Corporation Pharmaceutical compositions
USRE34313E (en) * 1983-09-23 1993-07-13 National Research Development Corporation Pharmaceutical compositions

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0138420A2 (en) * 1983-09-23 1985-04-24 National Research Development Corporation Pharmaceutical compositions containing 1-hydroxypyrid-2-one derivatives
GB2146990A (en) * 1983-09-23 1985-05-01 Nat Res Dev 1-hydroxypyrid-2-ones
US4587240A (en) * 1983-09-23 1986-05-06 National Research Development Corp. Pharmaceutical compositions
EP0138420A3 (en) * 1983-09-23 1987-05-20 National Research Development Corporation Pharmaceutical compositions containing 1-hydroxypyrid-2-one derivatives
US4912118A (en) * 1983-09-23 1990-03-27 National Research Development Corporation Pharmaceutical compositions
US5104865A (en) * 1983-09-23 1992-04-14 National Research Development Corporation Iron complexes of hydroxypyridones useful for treating iron overload
USRE34313E (en) * 1983-09-23 1993-07-13 National Research Development Corporation Pharmaceutical compositions

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