GB1077696A - Substituted-5-nitroimidazoles - Google Patents

Substituted-5-nitroimidazoles

Info

Publication number
GB1077696A
GB1077696A GB3577766A GB3577766A GB1077696A GB 1077696 A GB1077696 A GB 1077696A GB 3577766 A GB3577766 A GB 3577766A GB 3577766 A GB3577766 A GB 3577766A GB 1077696 A GB1077696 A GB 1077696A
Authority
GB
United Kingdom
Prior art keywords
alkyl
formula
group
radical
aralkyl
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
GB3577766A
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.)
Merck and Co Inc
Original Assignee
Merck and Co 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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1077696A publication Critical patent/GB1077696A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/91—Nitro radicals
    • C07D233/92—Nitro radicals attached in position 4 or 5
    • C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Basic Packing Technique (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention comprises (1) compounds of formula <FORM:1077696/C2/1> in which R2 is a C1- 5 alkyl radical, or a radical of formula -(CH2)nOX0 where n is 2-4 and X0 is a C1- 6 alkanoyl group, and R is a univalent hydrocarbon radical, (2) the preparation of compounds of Formula I by treating a compound of formula <FORM:1077696/C2/2> with an oxidizing agent, and (3) the process which comprises reacting a compound of Formula I above in which R2 is a C1- 5 alkyl radical with cyanide ions in an aqueous reaction medium to produce a 1-alkyl-5-nitroimidazole-2-carboxamide. Certain of the 1-substituted-2-R-thio-5-nitroimidazole starting materials of Formula II may be prepared by reacting a 1-alkyl- or 1-hydroxyalkyl-2-mercaptoimidazole with an alkyl iodide, alkyl sulphate, aralkyl iodide, or diphenyl-iodonium iodide to introduce an alkyl, aralkyl or phenyl group, and nitrating the 1-alkyl- or 1 - hydroxyalkyl - 2 - R - thio - imidazole formed (where R is an alkyl, aralkyl or phenyl group), and, when R2 is a hydroxyalkyl group, converting this group to a (C1- 6 alkanoyloxy) alkyl group.
GB3577766A 1963-08-07 1964-08-04 Substituted-5-nitroimidazoles Expired GB1077696A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US30067563A 1963-08-07 1963-08-07

Publications (1)

Publication Number Publication Date
GB1077696A true GB1077696A (en) 1967-08-02

Family

ID=23160128

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3577766A Expired GB1077696A (en) 1963-08-07 1964-08-04 Substituted-5-nitroimidazoles
GB3156964A Expired GB1077692A (en) 1963-08-07 1964-08-04 Imidazole derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB3156964A Expired GB1077692A (en) 1963-08-07 1964-08-04 Imidazole derivatives

Country Status (11)

Country Link
BE (1) BE651423A (en)
BR (1) BR6461527D0 (en)
CH (1) CH467266A (en)
DE (1) DE1470080A1 (en)
DK (4) DK108499C (en)
FR (1) FR1583154A (en)
GB (2) GB1077696A (en)
IL (2) IL29324A (en)
NL (2) NL139524B (en)
NO (1) NO116163B (en)
SE (1) SE325273B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3676439A (en) * 1971-04-13 1972-07-11 Hoffmann La Roche 5,6-dihydro-8,8-dimethyl-3-nitro-8h imidazo(2-1-c) (1,4)oxazine
DE102022003986A1 (en) 2021-10-01 2023-04-06 Tobias Schmallenbach Multifunctional bag

Also Published As

Publication number Publication date
FR1583154A (en) 1969-10-24
IL29324A (en) 1968-08-22
SE325273B (en) 1970-06-29
DK108229C (en) 1967-10-23
NL139524A (en)
NO116163B (en) 1969-02-10
DK108499C (en) 1967-12-27
DE1470080A1 (en) 1970-01-02
BE651423A (en) 1965-02-05
BR6461527D0 (en) 1973-07-17
NL6409120A (en) 1965-02-08
CH467266A (en) 1969-01-15
DK109264C (en) 1968-04-08
NL139524B (en) 1973-08-15
IL21758A (en) 1968-08-22
DK108153C (en) 1967-09-25
GB1077692A (en) 1967-08-02

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