GB1240392A - Halo substituted uracils and hydrouracils and preparation of same - Google Patents

Halo substituted uracils and hydrouracils and preparation of same

Info

Publication number
GB1240392A
GB1240392A GB27119/69A GB2711969A GB1240392A GB 1240392 A GB1240392 A GB 1240392A GB 27119/69 A GB27119/69 A GB 27119/69A GB 2711969 A GB2711969 A GB 2711969A GB 1240392 A GB1240392 A GB 1240392A
Authority
GB
United Kingdom
Prior art keywords
alkoxy
alkyl
halogen
uracil
halo
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
GB27119/69A
Inventor
Albert William Lutz
Bryant Leonidas Walworth
Richard William Feeny
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB1240392A publication Critical patent/GB1240392A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/60—Three or more oxygen or sulfur atoms

Landscapes

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

Abstract

1,240,392. Uracil derivatives. AMERICAN CYANAMID CO. 28 May, 1969 [17 June, 1968 (2); 5 March, 1969], No. 27119/69. Heading C2C. [Also in Division A5-] Compounds of formulµ wherein X is halogen or C 1 _ 4 alkyl, Y is halogen, R 1 is halogen, hydroxy, C 1 _ 6 alkoxy or mono- or dihalo- C 1 _ 6 alkoxy, R 2 is hydrogen, C 1 _ 6 alkyl optionally substituted by halogen, hydroxy or C 1 _ 4 alkoxy groups, C 2 _ 6 alkenyl, cyclohexyl, or phenyl optionally substituted by nitro, halogen, C 1 _ 4 alkoxy, mono- or di halo- C 1 _ 4 alkoxy or trifluoromethyl groups, R 3 is hydrogen; C 1 _ 4 alkyl, halo, C 1 _ 4 alkoxy, cyano, thiocyano, nitro or C 1 _ 4 alkylthio and R 4 is or optionally substituted C 1 _ 12 alkyl, C 2 _ 6 alkenyl; C 3 _ 8 cycloalkyl, phenyl or benzyl, the substituents being selected from halo, nitro, amino, C 1 _ 4 alkyl, halo- C 1 _ 4 alkyl, C 1 _ 4 alkoxy, carboxy or carb-C 1 _ 4 - alkoxy groups, and water-soluble salts thereof, are prepared by (a) formation of a uracil wherein R 3 is hydrogen by reaction of'a compound of formula CF 3 C(NH 2 ) = CR 3 COOR 5 , wherein R 5 is. C 1 _ 4 alkyl, with an isocyanate R 4 NCO, (b) introduction of a substituent R 3 by known methods, or (c) , conversion of a uracil to a hydrouracil by reaction with halogen inthe presence of water or a C 1 _ 6 alkanol or haloalkanol, followed optionally by replacement of a hydroxy substituent R 1 by a halogen atom. Alkoxy substituents R 3 in uracils may be introduced by reaction of a compound CF 3 C(NH 2 )= CHCOOR 5 with an isothiocyanate R 4 NCS to form a thiouracil, reacting this with bromine to form a 2,2<SP>1</SP>- dithiobis - (5 - bromo - 4 - pyrimidone), treating this with a sodium alkoxide and zinc dust to form a 5 - alkoxy - 2 - thiouracil and treating this with chloroacetic and to form a 5-alkoxy-uracil. The products have, herbicidal activity. 5 - Bromo - 6 - trifluoromethyl - uracil is prepared by bromination.
GB27119/69A 1968-06-17 1969-05-28 Halo substituted uracils and hydrouracils and preparation of same Expired GB1240392A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US73730868A 1968-06-17 1968-06-17
US73728868A 1968-06-17 1968-06-17
US80470869A 1969-03-05 1969-03-05

Publications (1)

Publication Number Publication Date
GB1240392A true GB1240392A (en) 1971-07-21

Family

ID=27419225

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27119/69A Expired GB1240392A (en) 1968-06-17 1969-05-28 Halo substituted uracils and hydrouracils and preparation of same

Country Status (10)

Country Link
BE (1) BE742508A (en)
CH (1) CH523259A (en)
DE (1) DE1930776A1 (en)
DK (1) DK132682C (en)
ES (2) ES368447A1 (en)
FR (1) FR2011113A1 (en)
GB (1) GB1240392A (en)
IL (1) IL32279A (en)
NL (1) NL6909144A (en)
SE (1) SE379043B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5077297A (en) * 1988-04-22 1991-12-31 Imperial Chemical Industries Plc Novel compounds
US5104878A (en) * 1989-04-17 1992-04-14 Imperial Chemical Industries Plc 1-phenyl-6-one-pyrimidine derivatives
US9763882B2 (en) 2011-03-10 2017-09-19 Ferring Bv Composition for the treatment of fistula

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5077297A (en) * 1988-04-22 1991-12-31 Imperial Chemical Industries Plc Novel compounds
US5104878A (en) * 1989-04-17 1992-04-14 Imperial Chemical Industries Plc 1-phenyl-6-one-pyrimidine derivatives
US9763882B2 (en) 2011-03-10 2017-09-19 Ferring Bv Composition for the treatment of fistula
US10617644B2 (en) 2011-10-03 2020-04-14 Ferring B.V. Composition for the treatment of fistula

Also Published As

Publication number Publication date
IL32279A0 (en) 1969-07-30
ES370564A1 (en) 1971-04-16
NL6909144A (en) 1969-12-19
DK132682C (en) 1976-06-28
SE379043B (en) 1975-09-22
DK132682B (en) 1976-01-26
FR2011113A1 (en) 1970-02-27
CH523259A (en) 1972-05-31
IL32279A (en) 1973-01-30
DE1930776A1 (en) 1970-01-02
ES368447A1 (en) 1971-05-01
BE742508A (en) 1970-06-02

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