Patent ID: 6172231
Filing Date: 2001-01-09
Classification: C07D

Abstract:
A process for preparing a compound of Formula I: ##STR36##wherein: ##STR37##represents:a) 6-membered heterocyclyl containing one, two or three double bonds, but at least one double bond and 1 heteroatom selected from N, the heterocyclyl is unsubstituted or substituted with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, N(R.sup.5).sub.2, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, CO(CH.sub.2).sub.n CH.sub.3, and CO(CH.sub.2).sub.n CH.sub.2 N(R.sup.5).sub.2,C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, or C.sub.3 -C.sub.8 cycloalkyl, are unsubstituted one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, N(R.sup.5).sub.2, C.sub.1 -C.sub.8 alkoxy, C.sub.3 -C.sub.8 cycloalkyl, CO(CH.sub.2).sub.n CH.sub.3, and CO(CH.sub.2).sub.n CH.sub.2 N(R.sup.5).sub.2,aryl is defined as phenyl or naphthyl, which is unsubstituted or substituted with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, N(R.sup.5).sub.2, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, CO(CH.sub.2).sub.n CH.sub.3, CO(CH.sub.2).sub.n CH.sub.2 N(R.sup.5).sub.2, or when aryl is substituted on adjacent carbons they can form a 5- or 6-membered fused ring having one, two or three heteroatoms selected from O, N, and S, this ring is unsubstituted or substituted on carbon or nitrogen with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.6, Br, Cl, F, I, CF.sub.3, N(R.sup.7).sub.2, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, CO(CH.sub.2).sub.n CH.sub.3, and CO(CH.sub.2).sub.n CH.sub.2 N(R.sup.5).sub.2 ;R.sup.2 is: OR.sup.4 or N(R.sup.5).sub.2 ;R.sup.3 is:a) H,b) C.sub.1 -C.sub.8 alkyl,c) C.sub.1 -C.sub.8 alkoxyl,d) C.sub.3 -C.sub.7 cycloalkyl,e) S(O).sub.t R.sup.5,f) Br, Cl, F, I,g) aryl,h) heteroaryl,i) N(R.sup.5).sub.2,j) NH.sub.2,k) --CHO,l) --CO--C.sub.1 -C.sub.8 alkyl,m) --CO-aryl,n) --CO-heteroaryl,o) --CO.sub.2 R.sup.4, orp) protected aldehyde;heteroaryl is defined as a 5- or 6-membered aromatic ring containing 1, 2 or 3 heteroatoms selected from O, N and S , which is unsubstituted or substituted with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, N(R.sup.5).sub.2, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, CO(CH.sub.2).sub.n CH.sub.3, and CO(CH.sub.2).sub.n CH.sub.2 N(R.sup.5).sub.2,m is: 2;n is: 0 to 5;t is: 0, 1 or 2;R.sup.4 is: H, or C.sub.1 -C.sub.8 alkyl;R.sup.5 is: H, or C.sub.1 -C.sub.8 alkyl, or aryl;R.sup.6, is: H, C.sub.1 -C.sub.8 alkyl, or aryl;R.sup.7 is: H, C.sub.1 -C.sub.8 alkyl, aryl, which is unsubstituted or substituted with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, N(R.sup.5).sub.2, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.8 cycloalkyl, CO(CH.sub.2).sub.n CH.sub.3, CO(CH.sub.2).sub.n CH.sub.2 N(R.sup.5).sub.2 ; or when two R.sup.7 substutients are on the same nitrogen they can join to form a ring of 3 to 6 atom; andR.sup.8, R.sup.9, R.sup.10 and R.sup.11 are independently: H, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkynyl, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkylthio, aryl, each of which is unsubstituted or substituted with one, two or three substituents selected from the group consisting of: OH, CO.sub.2 R.sup.4, Br, Cl, F, I, CF.sub.3, N(R.sup.5).sub.2, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, CO(CH.sub.2).sub.n CH.sub.3, or CO(CH.sub.2).sub.n CH.sub.2 N(R.sup.5).sub.2 ;comprising reacting a compound of Formula II in a solvent, ##STR38##with a solution of periodic acid, a catalytic amount of a chromium reagent in a solvent at a temperature range of about -20.degree. C. to about 40.degree. C. for about 15 minutes to about 24 hours to oxidize to the compound of Formula I.