Process for preparing spirocyclic tetronic acid derivatives

A process for preparing a compound of the formula (I)

• wherein
• X represents C1-C6-alkyl, halogen, C1-C6-alkoxy or C1-C3-halogenoalkyl,
• Y represents hydrogen, C1-C6-alkyl, halogen, C1-C6-alkoxy or C1-C3-halogenoalkyl,
• Z represents C1-C6-alkyl, halogen or C1-C6-alkoxy,
• n represents a number from 0 to 3,
• or the radicals X and Z together with the phenyl radical to which they are attached form a naphthalene radical of the formula
• in which Y is defined as above,
• A represents optionally halogen-substituted C1-C12-alkyl, C2-C8-alkenyl, C1-C10-alkoxy-C1-C8-alkyl, represents optionally halogen-, C1-C6-alkyl- or C1-C6-alkoxy-substituted C3-C8-cycloalkyl, in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and/or sulphur or represents optionally halogen-, C1-C6-alkyl-, C1-C6-halogenoalkyl-, C1-C6-alkoxy-, C1-C6-halogenoalkoxy-, cyano- or nitro-substituted phenyl or phenyl-C1-C6-alkyl,
• B represents C1-C12-alkyl or C1-C8-alkoxy-C1-C6-alkyl or
• A, B and the carbon atom to which they are attached represent C5-C10-cycloalkyl or C5-C10-cycloalkenyl in which optionally one methylene group is replaced by oxygen or sulphur and which are optionally substituted by C1-C8-alkyl, C3-C10-cycloalkyl, C1-C8-halogenoalkyl, C1-C8-alkoxy, C1-C8-alkylthio, halogen or phenyl or
• A, B and the carbon to which they are attached represent C5-C8-cycloalkyl or C5-C8-cycloalkenyl in which two carbon atoms are attached to one another by optionally C1-C6-alkyl-, C1-C6-alkoxy- or halogen-substituted C3-C6-alkanediyl, C3-C6-alkenediyl or C4-C6-alkanedienediyl in which optionally one methylene group is replaced by oxygen or sulphur,
• R1 represents optionally halogen-substituted C1-C20-alkyl, C1-C20-alkoxy, C2-C20-alkenyl, C3-C10-alkenyloxy, C1-C8-alkoxy-C1-C8-alkyl, C1-C8-alkylthio-C1-C8-alkyl, optionally C1-C6-alkyl-, C1-C6-alkoxy-, fluorine- or chlorine-substituted cycloalkyl having 3 to 8 ring atoms which may be interrupted by oxygen and/or sulphur atoms,
• represents optionally halogen-, nitro-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-halogenoalkyl- or C1-C6-halogenoalkoxy-substituted phenyl or phenoxy;
• represents optionally halogen-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-halogenoalkyl-, C1-C6-halogenoalkoxy-substituted phenyl-C1-C6-alkyl or phenyl-C1-C4-alkyloxy,
• represents optionally halogen- or C1-C6-alkyl-substituted hetaryl,
• represents optionally halogen- or C1-C6-alkyl-substituted phenoxy-C1-C6-alkyl,
• represents optionally halogen-, amino- or C1-C6-alkyl-substituted hetaryloxy-C1-C6-alkyl,
• said process comprising deprotonating with a base a compound of the formula (II)
• wherein
• X, Y, Z, n, A and B are as defined above and
• R8 represents C1-C6-alkyl;
• reacting the deprotonated compound with a compound of the formula (III)
• wherein
• R1 is as defined above and
• Hal represents chlorine or bromine;
• and
• collecting the reaction product.

A process for preparing a compound of the formula (I)

• wherein
• X represents C1-C4-alkyl, fluorine, chlorine, bromine, C1-C4-alkoxy or C1-C2-halogenoalkyl,
• Y represents hydrogen, C1-C4-alkyl, fluorine, chlorine, bromine, C1-C4-alkoxy or C1-C2-halogenoalkyl,
• Z represents C1-C4-alkyl, fluorine, chlorine, bromine or C1-C4-alkoxy,
• n represents a number from 0 to 2,
• A, B and the carbon atom to which they are attached represent C5-C8-cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur and which is optionally substituted by C1-C6-alkyl, C1-C3-halogenoalkyl, C1-C6-alkoxy, fluorine or chlorine, or
• A, B and the carbon atom to which they are attached represent C5-C6-cycloalkyl in which two carbon atoms are attached to one another by optionally C1-C4-alkyl-, C1-C4-alkoxy-, fluorine-, chlorine- or bromine-substituted C3-C5-alkanediyl, C3-C5-alkenediyl, in which optionally one methylene group is replaced by oxygen or sulphur, or attached to one another by butadienediyl,
• R1 represents optionally fluorine- or chlorine-substituted C1-C16-alkyl, C1-C16-alkoxy, C3-C6-alkenyloxy, C2-C16-alkenyl, C1-C6-alkoxy-C1-C4-alkyl, C1-C6-alkylthio-C1-C4-alkyl, optionally methyl-, ethyl-, methoxy-, fluorine- or chlorine-substituted cycloalkyl having 3 to 7 ring atoms which may be interrupted by 1 or 2 oxygen and/or sulphur atoms,
• represents optionally fluorine-, chlorine-, bromine-, nitro-, C1-C4-alkyl-, C1-C4-alkoxy-, C1-C3-halogenoalkyl- or C1-C3-halogenoalkoxy-substituted phenyl, phenoxy or benzyloxy,
• represents optionally halogen- or C1-C6-alkyl-substituted hetaryl,
• said process comprising deprotonating with a base a compound of the formula (II)
• wherein
• X, Y, Z, n, A and B are as defined above and
• R8 represents C1-C4-alkyl;
• reacting the deprotonated compound with a compound of the formula (III)
• wherein
• R1 and Hal are as defined above;
• and
• collecting the reaction product.

A process for preparing a compound of the formula (I)

• wherein
• X represents methyl, ethyl, propyl, i-propyl, fluorine, chlorine, bromine, methoxy, ethoxy or trifluoromethyl,
• Y represents hydrogen, methyl, ethyl, propyl, i-propyl, butyl, i-butyl, tert-butyl, fluorine, chlorine, bromine, methoxy, ethoxy or trifluoromethyl,
• Z represents methyl, ethyl, i-propyl, butyl, i-butyl, tert-butyl, fluorine, chlorine, bromine, methoxy or ethoxy,
• n represents the number 0 to 1,
• A, B and the carbon atom to which they are attached represent C3-C8-cycloalkyl in which optionally one methylene group is replaced by oxygen or sulphur and which is optionally substituted by methyl, ethyl, n-propyl, iso-propyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, iso-propoxy, butoxy or iso-butoxy,
• R1 represents optionally fluorine- or chlorine-substituted C1-C14-alkyl, C1-C10-alkoxy, C2-C14-alkenyl, C3-C6-alkenyloxy, C1-C4-alkoxy-C1-C2-alkyl, C1-C4-alkylthio-C1-C2-alkyl or cycloalkyl having 3 to 6 ring atoms which may be interrupted by 1 or 2 oxygen and/or sulphur atoms,
• represents optionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, propyl-, i-propyl-, methoxy-, ethoxy-, trifluoromethyl-, trifluoromethoxy-, nitro-substituted phenyl, phenoxy or benzyloxy;
• represents optionally chlorine-, methyl- or ethyl-substituted pyridyl,
• said process comprising deprotonating with a base a compound of the formula (II)
• wherein
• X, Y, Z, n, A and B are as defined above and
• R8 represents methyl, ethyl, propyl or iso-propyl;
• reacting the deprotonated compound with a compound of the formula (III)
• wherein
• R1 and Hal are as defined above;
• and
• collecting the reaction product.