GB1215815A - Production of quinoxaline-di-n-oxides and benzimidazole mono- and di-n-oxides - Google Patents

Production of quinoxaline-di-n-oxides and benzimidazole mono- and di-n-oxides

Info

Publication number
GB1215815A
GB1215815A GB5787467A GB5787467A GB1215815A GB 1215815 A GB1215815 A GB 1215815A GB 5787467 A GB5787467 A GB 5787467A GB 5787467 A GB5787467 A GB 5787467A GB 1215815 A GB1215815 A GB 1215815A
Authority
GB
United Kingdom
Prior art keywords
oxides
benzimidazole
group
hydroxy
quinoxaline
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
GB5787467A
Inventor
Costas Hercules Issidorides
Makhluf Jeryies Haddadin
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.)
Research Corp
Original Assignee
Research Corp
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 Research Corp filed Critical Research Corp
Priority to GB5787467A priority Critical patent/GB1215815A/en
Publication of GB1215815A publication Critical patent/GB1215815A/en
Priority to MY195/73A priority patent/MY7300195A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/22—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms directly attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
    • C07D241/52—Oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1,215,815. Quinoxaline and benzimidazole N- oxides. RESEARCH CORP. 20 Dec., 1967, No. 57874/67. Heading C2C. A process for producing quinoxaline di-N- oxides, benzimidazole-di-N-oxides and 1-hydroxybenzimidazole-3-oxides comprises reacting an isobenzofuroxan with a compound containing a methylene group which is activated by two electron withdrawing groups or a compound containing a methylene group which is activated by one electron withdrawing group, said one electron withdrawing group being a nitro group or a carbonyl group of a ketone or an aldehyde, in the presence of a base with the proviso in some cases that when a keto group is present in the molecule said base is not ammonia nor a primary aliphatic or cycloaliphatic amine. Examples of such compounds containing activated methylene groups include ketones, aldehydes, #-diketones, #-keto ester, malonic esters and nitroalkanes. The B ring of the heterocycle may be substituted by alkyl, cycloalkyl, aryl, aralkyl, alkoxy, carboxy, esterified carboxy, acyl, carboxyamide, cyano, amino, amide, oximino methyl, formyl and formyl-dimethyl acetal groups. The A ring may be substituted by alkyl, acyl, trifluoromethyl groups or halogen atoms. The following quinoxaline di-N-oxides, stated to be novel, are thus prepared; 2-cyano-3- amino; 2-formyldimethyl acetal; 2-carboethoxy - 3 - formyldiethylacetal; 2 - carbomethoxy - 3 - hydroxy; 2 - carboethoxy - 3- hydroxy -; 2 - carboethoxymethyl - 3 - methyl; 2 - carbomethoxymethyl - 3 - carbomethoxy -; 2 - (2<SP>1</SP> - diethylaminoethylene. The following, also stated to be novel, are prepared: 1-hydroxy - 2 - carboethoxybenzimidazole - 3 - oxide, 1 - hydroxy - 2 - benzimidazole - propionamide- 3 - oxide, 2,2 - dimethyl - 2H - benzimidazole- 1,3 - dioxide, 2,2 - pentamethylene - 2H - benzimidazole-1,3-dioxide.
GB5787467A 1967-12-20 1967-12-20 Production of quinoxaline-di-n-oxides and benzimidazole mono- and di-n-oxides Expired GB1215815A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB5787467A GB1215815A (en) 1967-12-20 1967-12-20 Production of quinoxaline-di-n-oxides and benzimidazole mono- and di-n-oxides
MY195/73A MY7300195A (en) 1967-12-20 1973-12-30 Production of quinoxaline-di-n-oxides and benzimidazole mono-and di-n-oxides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5787467A GB1215815A (en) 1967-12-20 1967-12-20 Production of quinoxaline-di-n-oxides and benzimidazole mono- and di-n-oxides

Publications (1)

Publication Number Publication Date
GB1215815A true GB1215815A (en) 1970-12-16

Family

ID=10480250

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5787467A Expired GB1215815A (en) 1967-12-20 1967-12-20 Production of quinoxaline-di-n-oxides and benzimidazole mono- and di-n-oxides

Country Status (2)

Country Link
GB (1) GB1215815A (en)
MY (1) MY7300195A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3846425A (en) * 1970-04-02 1974-11-05 Bayer Ag New imines, their preparation and their pharmaceutical use
USB399098I5 (en) * 1970-04-02 1976-02-24
US3983235A (en) * 1970-04-02 1976-09-28 Bayer Aktiengesellschaft Veterinary feedstuffs
US3983236A (en) * 1970-04-02 1976-09-28 Bayer Aktiengesellschaft Veterinary feedstuffs
US3984550A (en) * 1970-04-02 1976-10-05 Bayer Aktiengesellschaft Veterinary feedstuffs
US3984547A (en) * 1970-04-02 1976-10-05 Bayer Aktiengesellschaft Veterinary feedstuffs
US3984553A (en) * 1970-04-02 1976-10-05 Bayer Aktiengesellschaft Veterinary feedstuffs
US4264600A (en) 1978-10-20 1981-04-28 Eli Lilly And Company Treatment of influenza with 2-estersubstituted-3,4-dihydro-3-oxoquinoxalines
WO2018109504A1 (en) * 2016-12-16 2018-06-21 Universitetet I Oslo N-oxide heterocycles for use in the treatment of cancer and bacterial diseases

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3846425A (en) * 1970-04-02 1974-11-05 Bayer Ag New imines, their preparation and their pharmaceutical use
US3846414A (en) * 1970-04-02 1974-11-05 Bayer Ag New imines, their preparation and their pharmaceutical use
US3856957A (en) * 1970-04-02 1974-12-24 Bayer Ag Methods and compositions for treating bacterial infections employing imines
USB399098I5 (en) * 1970-04-02 1976-02-24
US3983235A (en) * 1970-04-02 1976-09-28 Bayer Aktiengesellschaft Veterinary feedstuffs
US3983236A (en) * 1970-04-02 1976-09-28 Bayer Aktiengesellschaft Veterinary feedstuffs
US3984550A (en) * 1970-04-02 1976-10-05 Bayer Aktiengesellschaft Veterinary feedstuffs
US3984547A (en) * 1970-04-02 1976-10-05 Bayer Aktiengesellschaft Veterinary feedstuffs
US3984553A (en) * 1970-04-02 1976-10-05 Bayer Aktiengesellschaft Veterinary feedstuffs
US3997665A (en) * 1970-04-02 1976-12-14 Bayer Aktiengesellschaft Veterinary feedstuffs
US4264600A (en) 1978-10-20 1981-04-28 Eli Lilly And Company Treatment of influenza with 2-estersubstituted-3,4-dihydro-3-oxoquinoxalines
WO2018109504A1 (en) * 2016-12-16 2018-06-21 Universitetet I Oslo N-oxide heterocycles for use in the treatment of cancer and bacterial diseases
US11046678B2 (en) 2016-12-16 2021-06-29 Pål Rongved Substituted phenazines and methods of treating cancer and bacterial diseases
US11958842B2 (en) 2016-12-16 2024-04-16 Adjutec Pharma As Substituted phenazines and methods of treating cancer and bacterial diseases

Also Published As

Publication number Publication date
MY7300195A (en) 1973-12-31

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