GB765529A - Tetrahydrofuran derivatives and their conversion to pyridine diols - Google Patents

Tetrahydrofuran derivatives and their conversion to pyridine diols

Info

Publication number
GB765529A
GB765529A GB434655A GB434655A GB765529A GB 765529 A GB765529 A GB 765529A GB 434655 A GB434655 A GB 434655A GB 434655 A GB434655 A GB 434655A GB 765529 A GB765529 A GB 765529A
Authority
GB
United Kingdom
Prior art keywords
alkoxy
conversion
carbamyltetrahydrofurans
pyridinediol
preparation
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
GB434655A
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
Priority to GB434655A priority Critical patent/GB765529A/en
Publication of GB765529A publication Critical patent/GB765529A/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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
    • C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

The invention comprises 2 : 5-di-(C1-C6)-alkoxy - 2 - carbamyltetrahydrofurans and their conversion to 2 : 3-pyridinediols by reaction with an aqueous medium having a pH value not exceeding 7. The above tetrahydrofurans may be substituted by alkyl, cycloalkyl, aryl and/or aralkyl radicals in the 3-, 4- and 5-positions, while "alkoxy" includes methoxy, ethoxy, propoxy, butoxy, amyloxy and hexyloxy. The 2 : 5-di-(C1-C6)-alkoxy-2-carbamyltetrahydrofurans are prepared by reacting an ester (preferably a methyl ester) of a corresponding 2 : 5 - di - (C1-C6) - alkoxy - tetrahydrofuroic acid with ammonia. The conversion to the 2 : 3-pyridinediol is preferably effected at atmospheric pressure under reflux temperatures between 60-120 DEG C. and in presence of hydrochloric, sulphuric or acetic acids. The examples describe the preparation of 2 : 5-dimethoxy-2-carbamyltetrahydrofuran and 2 : 3-pyridinediol. The preparation of n-cetyl-(2 : 3-dihydroxy-pyridinium) chloride is also referred to.
GB434655A 1955-02-14 1955-02-14 Tetrahydrofuran derivatives and their conversion to pyridine diols Expired GB765529A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB434655A GB765529A (en) 1955-02-14 1955-02-14 Tetrahydrofuran derivatives and their conversion to pyridine diols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB434655A GB765529A (en) 1955-02-14 1955-02-14 Tetrahydrofuran derivatives and their conversion to pyridine diols

Publications (1)

Publication Number Publication Date
GB765529A true GB765529A (en) 1957-01-09

Family

ID=9775450

Family Applications (1)

Application Number Title Priority Date Filing Date
GB434655A Expired GB765529A (en) 1955-02-14 1955-02-14 Tetrahydrofuran derivatives and their conversion to pyridine diols

Country Status (1)

Country Link
GB (1) GB765529A (en)

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