Process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives

Process for the preparation of 5-substituted 1-alkyltetrazolyl oxime derivatives of the general formula (I)

• in which
• R1 is alkyl, or phenyl optionally monosubstituted by halogen, cyano, nitro, C1-C8-alkyl, C1-C8-alkoxy, methylsulphonyl, trifluoromethyl or aryl,
• R2 is C1-C12-alkyl, C1-C12-haloalkyl or an alkoxyalkyl of the formula -[A-O]m—B,
• A is C2-C4-alkanediyl(alkylene),
• B is C1-C6-alkyl,
• m is 1 or 2,
• R3 is a pyridinyl group (Het1) or a thiazolyl group (Het2)
• in which
• R is hydrogen or halogen,
• Z is hydrogen, halogen, in each case substituted or unsubstituted C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, or the group —N(Ra)C(═O)Q,
• Q is hydrogen, in each case substituted or unsubstituted C1-C8-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkenyl-C1-C8alkyl, C3-C8-halocycloalkyl having 1 to 5 halogen atoms, C3-C8-cycloalkyl-C1-C8-alkyl, C3-C8-cycloalkenyl, C2-C8-alkenyl, C2-C8-haloalkenyl having 1 to 5 halogen atoms, C2-C8-alkynyl, C2-C8-haloalkynyl having 1 to 5 halogen atoms, C1-C8-alkoxy, C1-C8-haloalkoxy having 1 to 5 halogen atoms, C1-C8-halalkoxyalkyl having 1 to 5 halogen atoms, C2-C8-alkenyloxy, C2-C8-haloalkenyloxy having 1 to 5 halogen atoms C3-C8-alkynyloxy, C3-C8-haloalkynyloxy having 1 to 5 halogen atoms, C1-C8-alkylamino, (C1-C6-alkoxyimino)C1-C6-alkyl, (C1-C6-alkenyloxyimino)-C1-C6-alkyl, (C1-C6-alkinyloxyimino)-C1-C6-alkyl, (benzyloxyimino)-C1-C6-alkyl, C1-C8-alkylsulphenyl, arylsulphenyl, tri(C1-C8-alkyl)silyl-C1-C8-alkyl, tri(C1-C8-alkyl)silyloxy, tri(C1-C8alkyl)silyl-C3-C8-cycloalkyl, aryl, phenoxy, phenoxyalkyl, benzyloxy, heterocyclyl, C5-C12-bicycloalkyl, C5-C12-bicycloalkenyl, benzo-fused C5-C12-carbocyclyl,
• Ra is hydrogen, in each case substituted or unsubstituted C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, C2-C8-alkynyl, aryl, heterocyclyl,
• characterized in that
• (1) in a first step, oximes of the general formula (II)
• in which R1 and R2 have the meanings given above,
• are reacted with compounds of the general formula (III)
• in which
• R3 has the meanings given above and
• Y is chlorine, bromine, iodine, mesylate or tosylate,
• and the oxime ethers of the general formula (IV) obtained in this way
• in which R1, R2 and R3 have the meanings given above,
• (2) are reacted in a second step with perfluoroalkylsulphonic acid esters (R4—SO2-Oalkyl) or anhydrides [(R4—SO2)2O],
• and the compounds of the general formula (V) obtained in this way
• in which
• R1, R2 and R3 have the meanings given above and
• R4 is perfluoroalkyl,
• (3) are reacted in a third step with azides of the formula R5—N3.