Patent ID: 6951948

Claim:
A method of synthesizing highly substituted azole compounds having the general formula (Ia): wherein X is selected from the group consisting of NH, NR A wherein R A is hydrogen or —R wherein R is aralkyl; wherein is optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxy, alkyl, halogenated alkyl; alkenyl, cycloalkyl, alkoxy, aryl, aralkyl, amino, mono- or di-substituted amino, cyano nitro, —COOR, —COR, —SO 2 R and —CONR B R C ; wherein the amine substituents are independently selected from alkyl, cycloalkyl, aryl or aralkyl; wherein the cyclalkyl or aryl may be further optionally substituted with one or more substituent is independently selected from halogen, hydroxy, alkyl, halogenated alkyl, alkoxy, amino, mono- or di-substituted amino, cyano or nitro; Z is —OR A wherein R A is —CONR C R D : R 3 is selected from the group consisting of hydrogen, alkyl, aralkyl, cycloalkyl, and fluorinated alkyl; wherein the aralkyl may be optionally substituted with one or more substituents independently selected from halogen, hydroxy, alkyl, halogenated alkyl, alkoxy, amino, mono- or di-substituted amino, cyano or nitro; R 4 is selected from the group consisting of, alkyl, aryl, aralkyl, cycloalkyl, fluorinated alkyl, alkenyl, and alkynyl; wherein the alkyl, alkenyl, alkynyl, aryl or aralkyl may be optionally substituted with one or more substituents independently selected from halogen, hydroxy, alkyl, halogenated alkyl, alkoxy, aryl, amino, mono- or di-substituted amino, cyano or nitro; R is selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl, and fluorinated alkyl; wherein the aryl or aralkyl may be optionally substituted with one or more substituents independently selected from halogen, hydroxy, alkyl, halogenated alkyl, alkoxy, amino, mono- or di-substituted amino, cyano or nitro; R B is independently selected from the group consisting of hydrogen, —R, —COOR, —COR, —SO 2 R, —SOR and —CONR C R D ; R C and R D are independently selected from the group consisting of hydrogen, alkyl, aryl, aralkyl, cycloaralkyl, and fluorinated alkyl; wherein the aryl or aralkyl may be optionally substituted with one or more substituents independently selected from halogen, hydroxy, alkyl, halogenated alkyl, alkoxy, amino, mono- or di-substituted amino, cyano or nitro; which method comprises reacting a compound of formula (III) with a compound of formula (IV) wherein A is selected from F, Cl, Br or —OC(O)-t-butyl, and wherein V is a sterically hindered group, in a non-protic solvent; and then reacting with a compound of formula (V) wherein W is O, to form the corresponding compound of formula (Ic) and reacting the compound of formula (Ic) with a compound of formula (VI) Z—H (VI) to yield the corresponding compound of formula (Ia).