GB825241A - Antibacterial cyanonitrovinyl-benzenes and thiophenes - Google Patents

Antibacterial cyanonitrovinyl-benzenes and thiophenes

Info

Publication number
GB825241A
GB825241A GB1357257A GB1357257A GB825241A GB 825241 A GB825241 A GB 825241A GB 1357257 A GB1357257 A GB 1357257A GB 1357257 A GB1357257 A GB 1357257A GB 825241 A GB825241 A GB 825241A
Authority
GB
United Kingdom
Prior art keywords
cyano
bromo
hydrogen
cyanothiophene
vinylene
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
GB1357257A
Inventor
Alberto Vecchi
Gaetano Melone
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.)
Gruppo Lepetit SpA
Original Assignee
Lepetit SpA
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 Lepetit SpA filed Critical Lepetit SpA
Priority to GB1357257A priority Critical patent/GB825241A/en
Publication of GB825241A publication Critical patent/GB825241A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention comprises antibacterial compounds of the general formula <FORM:0825241/IV (b)/1> (wherein X represents sulphur or vinylene, R is hydrogen or, when X is vinylene, a nitro group, and R1 is hydrogen or bromine) and their preparation by reacting an aldehyde of the general formula <FORM:0825241/IV (b)/2> with an excess of nitromethane in the presence of alcoholic potash, refluxing the resulting mixture with acetic anhydride, and isolating the product either directly or after treatment with dilute hydrochloric acid. If required, the product so obtained (in which R1 is hydrogen) is reacted with two equivalents of bromine, and the resulting di-bromo derivative is dehydrobrominated, without isolation, with an equivalent of potassium carbonate. Examples describe the preparation of 4-cyano- and 4-cyano-b -bromo-b -nitrostyrene, 4-cyano- and 4-cyano-b - bromo - 2,b - dinitrostyrene, and 1 - (5 - cyano - 2 - thienyl) - and 1 - (5 - cyano - 2 - thienyl) - 2 - bromo - 2 - nitroethylene. 2 - Methyl - 5 - cyanothiophene, prepared by refluxing 2-methyl-5-iodothiophene with cuprous cyanide in pyridine, is oxidized in acetic acid with chromium trioxide/sulphuric acid to 2 - formyl - 5 - cyanothiophene di-acetate which is hydrolysed with sulphuric acid in aqueous ethanol to the aldehyde.
GB1357257A 1957-04-29 1957-04-29 Antibacterial cyanonitrovinyl-benzenes and thiophenes Expired GB825241A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1357257A GB825241A (en) 1957-04-29 1957-04-29 Antibacterial cyanonitrovinyl-benzenes and thiophenes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1357257A GB825241A (en) 1957-04-29 1957-04-29 Antibacterial cyanonitrovinyl-benzenes and thiophenes

Publications (1)

Publication Number Publication Date
GB825241A true GB825241A (en) 1959-12-09

Family

ID=10025388

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1357257A Expired GB825241A (en) 1957-04-29 1957-04-29 Antibacterial cyanonitrovinyl-benzenes and thiophenes

Country Status (1)

Country Link
GB (1) GB825241A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1203424B (en) * 1963-08-08 1965-10-21 Lilly Co Eli Preparations for combating microorganisms

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1203424B (en) * 1963-08-08 1965-10-21 Lilly Co Eli Preparations for combating microorganisms

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