Process for producing enyne derivatives

Details Process for producing enyne derivatives Process for producing enyne derivatives

C - Chemistry, Metallurgy

07

C

260/328.2, 260/4

C07C 209/68 (2006.01) C07C 209/08 (2006.01) C07C 211/23 (2006.01) C07C 211/29 (2006.01) C07C 211/30 (2006.01) C07C 213/08 (2006.01) C07C 215/50 (2006.01) C07C 217/46 (2006.01) C07D 333/00 (2006.01) C07D 333/16 (2006.01) C07D 333/20 (2006.01) C07D 333/62 (2006.01) C07F 7/10 (2006.01)

Patent

CA 2026599

A process for producing an enyne derivative of the formula: Image wherein R1 is a hydrogen atom, a lower alkyl group, a halo lower alkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group, R2 is a hydrogen atom or a group of the formula: Image wherein each of R3, R31 and R32 which may be the same or different, is a hydrogen atom or a lower alkyl group, each of R4, R5, R41 and R51 which may be the same or different, is a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group or a lower alkoxy group, R42 is a hydroxyl group, a halogen atom, a group of the formula B-O- (wherein B is a protecting group for a hydroxyl group), a hydroxymethyl group, a formyl group, a carboxyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, an amino group, a mercapto group or a group of the formula R6-X-Y- (wherein R6 is a phenyl or thienyl group which may have one or two substituents selected from the group consisting of a halogen atom, a hydroxyl group, a lower alkyl group, a cyano group, a lower alkoxy group and a heterocyclic group, each of X and Y which may be the same or different, is an oxygen atom, a sulfur atom, a carbonyl group, a group of the formula -CHR a- (wherein R a is a hydrogen atom or a lower alkyl group) or a group of the formula -NR b- (wherein R b is a hydrogen atom or a lower alkyl group), or X and Y together form a vinylene group or an ethynylene group), provided that when either one of X and Y is an oxygen atom, a sulfur atom or a group of the formula -NR b- (wherein R b is as defined above), the other is a carbonyl group or a group of the formula -CHR a- (wherein R a is as defined above), and R 7 is a lower alkyl or cycloalkyl group which may have a hydroxyl group or a lower alkoxy group, a phenyl group or a tri-lower alkylsilyl group, which process comprises reacting a compound of the formula: Z-CH2-CH=CH-W [I] wherein W is a halogen atom, and Z is a leaving group, with an amine of the formula: Image wherein R11 is a hydrogen atom, a lower alkyl group, a halo lower alkyl group, a lower alkenyl group, a lower alkynyl group or a cycloalkyl group, and R21 is a hydrogen atom or a group of the formula: Image wherein R3, R4, R5, R31, R32, R41, R42 and R51 are as defined above, if necessary in the presence of a base, to obtain a compound of he formula: Image wherein R11, R21 and W are as defined above, then reacting to this compound an acetylene derivative of the formula: HC.ident.C-R7 [V] wherein R7 is as defined above, in the presence of a palladium catalyst, to obtain a compound of the formula: Image wherein R11, R21 and R7 are as defined above, and, if necessary, N-alkylating this compound.

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