GB1419789A - 2-trifluoromethyl-4-quinolinols - Google Patents

2-trifluoromethyl-4-quinolinols

Info

Publication number
GB1419789A
GB1419789A GB3043974A GB3043974A GB1419789A GB 1419789 A GB1419789 A GB 1419789A GB 3043974 A GB3043974 A GB 3043974A GB 3043974 A GB3043974 A GB 3043974A GB 1419789 A GB1419789 A GB 1419789A
Authority
GB
United Kingdom
Prior art keywords
trifluoromethyl
alkyl
halogen
quinolinols
ethyl
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
GB3043974A
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.)
Pfizer Inc
Original Assignee
Pfizer 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 Pfizer Inc filed Critical Pfizer Inc
Publication of GB1419789A publication Critical patent/GB1419789A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

1419789 2 - Trifluoromethyl - 4 - quinolinols PFIZER Inc 11 Jan 1973 [2 Aug 1972] 30439/74 Divided out of 1419788 Heading C2C 2 - Trifluoromethyl - 4 - quinolinols of general formula or the alkali metal, ammonia and alkylamine salts thereof, wherein R 1 is H, halogen or C 1-4 alkyl; each of R 2 and R 3 is CN, NO 2 , CF 3 , C 1-5 acyl, S(O)R 4 , S(O) 2 R 4 , SO 2 NR 4 R 5 or CONR 4 R 5 in which R 4 and R 5 are each C 1-4 alkyl or R 2 is H, halogen or C 1-4 alkyl and R 3 is halogen or C 1-4 alkyl with the provisos that (a) when both R 1 and R 2 are H, R 3 is not a 6- or 8-position substituent and (b) when each of R 2 and R 3 is halogen or CH 3 and R 1 is H, R 2 and R 3 are not 6- and 8-position substituents, are prepared by condensation of the appropriate aniline derivative with ethyl 3-keto, 4,4,4-trifluorobutyrate or the appropriate ethyl-2-alkyl-3- keto-4,4,4-trifluoro butyrate in polyphosphonic acid at 100-200‹ C. Alternatively, the intermediate ethyl 3-anilino-trifluorocrotonate can be isolated and cyclized by heating in a suitable solvent at about 250‹ C. The 2-trifluoromethyl- 4-quinolinols in which R 1 = H can be chlorinated or brominated in the 3-position by reaction with SOCl 2 , Cl 2 or Br 2 . Amongst numerous examples compounds 6,8-dichloro-3-methyl-2- trifluoromethyl - 4 - quinolinol and 6 - nitro - 3- methyl - 2,8 - bis - (trifluoromethyl) - 4 - quinolinol are prepared. Herbicidal compositions comprise compounds of the above general formula and a carrier.
GB3043974A 1972-08-02 1973-01-11 2-trifluoromethyl-4-quinolinols Expired GB1419789A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US27731572A 1972-08-02 1972-08-02

Publications (1)

Publication Number Publication Date
GB1419789A true GB1419789A (en) 1975-12-31

Family

ID=23060321

Family Applications (2)

Application Number Title Priority Date Filing Date
GB162573A Expired GB1419788A (en) 1972-08-02 1973-01-11 Herbicidal method using 2-trifuluromethyl-4-quinolinols
GB3043974A Expired GB1419789A (en) 1972-08-02 1973-01-11 2-trifluoromethyl-4-quinolinols

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB162573A Expired GB1419788A (en) 1972-08-02 1973-01-11 Herbicidal method using 2-trifuluromethyl-4-quinolinols

Country Status (1)

Country Link
GB (2) GB1419788A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8697673B2 (en) 2011-03-31 2014-04-15 Pfizer Inc. Bicyclic pyridinones
US8916564B2 (en) 2012-09-21 2014-12-23 Pfizer Inc. Substituted pyrido[1,2-a]pyrazines for the treatment of neurodegenerative and neurological disorders
US9765073B2 (en) 2015-02-03 2017-09-19 Pfizer Inc. Cyclopropabenzofuranyl pyridopyrazinediones

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3210979A1 (en) * 1982-03-25 1983-09-29 Basf Ag, 6700 Ludwigshafen 3-CHLORINE-8-CYANO-CHINOLINE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR COMBATING UNWANTED PLANT GROWTH
DE3229175A1 (en) * 1982-08-05 1984-02-09 Basf Ag, 6700 Ludwigshafen 3,7-DICHLOR-8-CHINOLINE DERIVATIVES
FR2672596B1 (en) * 1991-02-07 1995-07-13 Roussel Uclaf NEW NITROGEN BICYCLIC DERIVATIVES, THEIR PREPARATION PROCESS, THE NEW INTERMEDIATES OBTAINED, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
FR2672597B1 (en) * 1991-02-07 1995-05-19 Roussel Uclaf NEW N-SUBSTITUTED QUINOLEIN DERIVATIVES, THEIR PREPARATION PROCESS, THE NEW INTERMEDIATES OBTAINED, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
FR2680510B1 (en) * 1991-08-20 1995-06-23 Roussel Uclaf NEW NITROGEN BICYCLIC DERIVATIVES, THEIR PREPARATION PROCESS, THE NEW INTERMEDIATES OBTAINED, THEIR APPLICATION AS MEDICAMENTS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
FR2672595B1 (en) * 1991-02-07 1995-05-19 Roussel Uclaf NOVEL NITROGEN BICYCLIC DERIVATIVES SUBSTITUTED BY A RADICAL BENZYL, THEIR PREPARATION PROCESS, THE NEW INTERMEDIATES OBTAINED, THEIR APPLICATION AS MEDICAMENTS.
EP0498722B1 (en) * 1991-02-07 1997-07-30 Roussel Uclaf Bicyclic nitrogen compounds, their preparation, intermediates obtained, their use as pharmaceuticals and pharmaceutical compositions containing them
FR2680511B1 (en) * 1991-08-20 1995-05-19 Roussel Uclaf N-SUBSTITUTED QUINOLEIN DERIVATIVES, THEIR PREPARATION PROCESS, INTERMEDIATES OBTAINED, THEIR APPLICATION AS MEDICAMENTS AND THE COMPOSITIONS CONTAINING THEM.
IL100555A (en) * 1991-02-07 2000-08-31 Hoechst Marion Roussel Inc N-substituted quinoline derivatives their preparation their use for the preparation of medicaments and the pharmaceutical compositions containing them
FR2684671B1 (en) * 1991-11-20 1995-05-19 Roussel Uclaf NEW QUINOLEIN DERIVATIVES, THEIR PREPARATION AND INTERMEDIATE PROCESSES AND THEIR APPLICATION AS MEDICAMENTS.
MX9200299A (en) * 1991-02-07 1992-12-01 Roussel Uclaf NEW NITROGENATED BICYCLE DERIVATIVES, THEIR PROCEDURE FOR PREPARING THE NEW INTERMEDIATE COMPOUNDS OBTAINED THEIR APPLICATION AS MEDICINES AND THE PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM.
FR2680509B1 (en) * 1991-08-20 1995-07-28 Roussel Uclaf NITROGEN BICYCLIC DERIVATIVES SUBSTITUTED BY A RADICAL BENZYL, THEIR PREPARATION PROCESS, THE INTERMEDIATES OBTAINED, THEIR APPLICATION AS MEDICAMENTS AND THE COMPOSITIONS CONTAINING THEM.
FR3132613A1 (en) * 2022-02-17 2023-08-18 Ecole Polytechnique Use of chromene or chroman derivatives as herbicidal agents

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8697673B2 (en) 2011-03-31 2014-04-15 Pfizer Inc. Bicyclic pyridinones
US9067934B2 (en) 2011-03-31 2015-06-30 Pfizer Inc. Bicyclic pyridinones
US8916564B2 (en) 2012-09-21 2014-12-23 Pfizer Inc. Substituted pyrido[1,2-a]pyrazines for the treatment of neurodegenerative and neurological disorders
US9193726B2 (en) 2012-09-21 2015-11-24 Pfizer Inc. Substituted pyrido[1,2-a]pyrazines for the treatment of neurodegenerative and neurological disorders
US9751877B2 (en) 2012-09-21 2017-09-05 Pfizer Inc. Substituted pyrido[1,2-a]pyrazines for the treatment of neurodegenerative and neurological disorders
US9765073B2 (en) 2015-02-03 2017-09-19 Pfizer Inc. Cyclopropabenzofuranyl pyridopyrazinediones

Also Published As

Publication number Publication date
GB1419788A (en) 1975-12-31

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee