SUBSTITUTED IMIDAZOPYRIDINES

专利名称：SUBSTITUTED IMIDAZOPYRIDINES发明人：LESLIE THOMAS ALLAN,GEOFFREY

TATTERSALL NEWBOLD,ALBERT PERCIVAL

申请号：US3609157D申请日：19680517公开号：US3609157A公开日：19710928

摘要：1,213,6. Fluorinated imidazopyridines. FISONS PEST CONTROL Ltd. 6 May,1968 [23 May, 1967], No. 23803/67. Heading C2C. [Also in Division A5] The inventioncomprises compounds of the general formula where one of the groups Z1, Z2, Z3 and Z4is a nitrogen atom and the other three groups are CR2, CR3 and CR4 respectively, where -R1 is selected from R5, -C(=A)BR5 and -SO 2 R6, where A is oxygen or sulphur, B is oxygenor sulphur or a single bond, R5 is alkenyl, alkynyl, substituted alkenyl, substitutedalkynyl, cycloaliphatic, substituted cycloaliphatic or heterocyclic, and R6 is alkyl,substituted alkyl, aryl, substituted aryl, alkenyl, alkynyl, aralkyl, substituted alkenyl,substituted alkynyl, substituted aralkyl, cycloaliphatic, substituted cycloaliphatic orheterocyclic, and where R2, R3 and R4 are the same or different and are selected fromhydrogen, alkyl, hydroxy, alkoxy, substituted alkoxy, aryloxy, substituted aryloxy, nitro,halogen, pseudohalogen, substituted alkyl, carboxy, carboxy ester, carboxy amide, N-substituted or di-substituted carboxy amide, amino, mono-or di-substituted amino, thiol,alkylthiol and oxygenated derivatives thereof, sulphonic acid and esters and amidesthereof, substituted sulphonic amides, and a heterocyclic ring attached to theimidazopyridine system through a nitrogen atom, and where X is trifluoromethyl or

pentafluoroethyl, and salts and N-oxides thereof. The compounds may be prepared by (i)reacting the corresponding substituted ortho-diaminopyridine or salt thereof, with atrihalogenoacetic acid or pentafluoropropionic acid or functional derivative thereofpreferably in a medium of an inorganic acid halide such as phosphorus oxychloride, and ifnecessary converting the trihalogen derivative to the trifluoro derivative by treatmentwith a metal fluoride; (ii) (when R1 is the group -COOR5) reacting the correspondingcompound wherein R1 is hydrogen with a chloroformate in the presence of a base e.g.triethylamine, or reacting an alkali metal salt of the corresponding imidazopyridinederivative with a chloroformate; or (iii) (when R1 is -SO 2 R6) reacting the correspondingcompound where R1 is hydrogen with a sulphonyl halide R6SO 2 D where D is halogen.Examples describe the preparation of 6-chloro-3-cyclohexyloxycarbonyl - 2 - trifluoro -methylimidazo (4,5-b) pyridine and the corresponding 6-nitro, 5-methyl and 5-cyanocompounds, 2-trifluoromethyl - 3 - benzyl - 6 - chloroimidazo (4,5-b) pyridine, 3 - allyl - 6 -chloro - 2 - trifluoromethylimidazo (4,5-b) pyridine, 3-propargyl-5- chloro-2-trifluoromethylimidazo (4,5-b) pyridine and 3-cyclohexyl-6-chloro-2-trifluoromethylimidazo (4,5-b) pyridine.

申请人：FISONS PEST CONTROL LTD.

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