Patent ID: 6172235
Filing Date: 2001-01-09
Classification: C07D,C07F

Abstract:
A process for the preparation of a compound of formula I: ##STR87##wherein ##STR88##represents:a) 5- or 6-membered heterocyclyl containing one, two or three double bonds, but at least one double bond and 1, 2 or 3 heteroatoms selected from O, N and S, 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.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkynyl, or 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,b) 5- or 6-membered carbocyclyl containing one or two double bonds, but at least one double bond, the carbocyclyl 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, or 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) aryl, wherein aryl is as defined below,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, or C.sub.3 -C.sub.8 cycloalkyl, are 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.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), 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, or 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, and when two substituents are located on adjacent carbons they can join to form a 5- or 6-membered ring with one, two or three heteroatoms selected from O, N, and S, which is unsubstituted or substituted with one, two or three substituents selected from the group consisting of: H, 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.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkynyl, or 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,n is 0 to 5;R.sup.1 is:a) 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,b) aryl, orc) heteroaryl;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.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkynyl, or 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 ; ##STR89##R.sup.3a is:a) CHO,b) --CO-C.sub.1 -C.sub.8 alkyl,c) --CO-aryl, ord) --CO-heteroaryl;X and Y are independently: O, S, or NR.sup.5 ;R.sup.4 is C.sub.1 -C.sub.8 alkyl;R.sup.5 is: C.sub.1 -C.sub.8 alkyl, or aryl; andR.sup.6, R.sup.7, R.sup.8 and R.sup.9 are independently: H, C.sub.1 -C.sub.8 alkyl, and aryl, such that either R.sup.6 and R.sup.7 are not the same and/or R.sup.8 and R.sup.9 are not the same, or R.sup.6 and R.sup.8 or R.sup.7 and R.sup.9 can join to form a 5- or 6-membered ring, 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, or 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 ;comprising reacting a .alpha.,.beta.-unsaturated ester or amide ##STR90##with an organolithium compound, R.sup.1 Li, in the presence of an aprotic solvent at a temperature range of about -78.degree. C. to about 0.degree. C.