GB1375163A - - Google Patents

Info

Publication number
GB1375163A
GB1375163A GB2955374A GB2955374A GB1375163A GB 1375163 A GB1375163 A GB 1375163A GB 2955374 A GB2955374 A GB 2955374A GB 2955374 A GB2955374 A GB 2955374A GB 1375163 A GB1375163 A GB 1375163A
Authority
GB
United Kingdom
Prior art keywords
prepared
alkoxy
compounds
alkyl
hydrogen
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
GB2955374A
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
Priority claimed from GB963871*[A external-priority patent/GB1375162A/en
Application filed filed Critical
Publication of GB1375163A publication Critical patent/GB1375163A/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
    • C07D239/24—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
    • 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
    • C07D239/48—Two nitrogen atoms
    • C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1375163 α-(benzyl)-acrylo and propio-nitriles WELLCOME FOUNDATION Ltd (Burroughs Wellcome Co) 20 Oct 1971 [22 Oct 1970 16 April 1971] 29553/74 and 29554/74 Divided out of 1375162 Heading C2C Novel compounds II in which R<SP>1</SP> and R<SP>3</SP> are C 2-4 alkyl, R<SP>2</SP> is C 1-12 alkyl or C 1-12 alkoxy and (a) X and Y represent an additional bond and Z is alkoxy, alkylthio or NR<SP>4</SP>R<SP>5</SP> which is an aliphatic or aromatic amino group or a tertiary amino group in which NR<SP>4</SP>R<SP>5</SP> from a heterocyclic ring system or (b) X is hydrogen and Y and Z are alkoxy or together are alkylenedioxy are prepared by reacting a benzaldehyde III with a #-substituted propionitrile (IV) (Z-CH 2 - CH 2 -CN) in which Z is alkoxy, alkylthio or NR<SP>4</SP>R<SP>5</SP> to give compound II in which X and Y represent an additional bond and when compounds II are required in which X is hydrogen and Y is alkoxy carrying the reaction out in the presence of an alkanol and an alkali-metal alkoxide. Compounds II in which R<SP>2</SP> is C 1-12 alkyl and X and Y are an additional bond and Z is NR<SP>4</SP>R<SP>5</SP> are prepared by reacting a compound V in which n is 1 or 2 and R<SP>2</SP> is C 1-12 alkyl with a #-substituted propionitrile (IV). Compounds II in which X is hydrogen and Y and Z are alkoxy may also be prepared by reduction of an α-(R<SP>1</SP>R<SP>2</SP>R<SP>3</SP>-benzylidene)-#-#dialkoxy propionitrile. Compounds prepared are those in which R<SP>1</SP> and R<SP>3</SP> are ethyl, R<SP>2</SP> is methyl or ethyl and Z is anilino and X, Y a bond or X is hydrogen and Y and Z methoxy. Compounds V are prepared by reacting an R<SP>1</SP>,R<SP>2</SP>,R<SP>3</SP>-substituted benzoate with dimethyl sulphone or sulphoxide and reducing the ketone produced. The benzoate is prepared by esterification of the corresponding acid which may be prepared by oxidation of an acetophenone prepared by Friedel-Crafts alkylation of p-alkylacetophenone. Benzaldehydes III are prepared by Rosamund reaction.
GB2955374A 1970-10-22 1974-07-03 Expired GB1375163A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB963871*[A GB1375162A (en) 1970-10-22 1970-10-22
GB963871 1971-04-16

Publications (1)

Publication Number Publication Date
GB1375163A true GB1375163A (en) 1974-11-27

Family

ID=26243063

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2955374A Expired GB1375163A (en) 1970-10-22 1974-07-03

Country Status (7)

Country Link
KR (1) KR780000097B1 (en)
DE (1) DE2152814A1 (en)
GB (1) GB1375163A (en)
HU (1) HU166528B (en)
PH (1) PH9226A (en)
RO (1) RO67383A (en)
SU (1) SU429581A3 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE792096A (en) * 1971-12-01 1973-05-30 Hoffmann La Roche NEW BENZYLPYRIMIDINES
GB1469521A (en) * 1973-01-05 1977-04-06 Wellcome Found Antimicrobial preparations

Also Published As

Publication number Publication date
DE2152814A1 (en) 1972-05-04
SU429581A3 (en) 1974-05-25
RO67383A (en) 1981-07-30
KR780000097B1 (en) 1978-04-08
PH9226A (en) 1975-07-15
HU166528B (en) 1975-03-28

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Legal Events

Date Code Title Description
416 Proceeding under section 16 patents act 1949
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee