Process for producing enyne derivatives

A process for producing an enyne derivative of the formula:

• ##STR17## wherein R.sup.1 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, R.sup.2 is a hydrogen atom or a group of the formula:
• ##STR18## wherein each of R.sup.3, R.sup.31 and R.sup.32 which may be the same or different, is a hydrogen atom or a lower alkyl group, each of R.sup.4, R.sup.5, R.sup.41 and R.sup.51 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, R.sup.42 is a hydroxyl group, a halogen atom, a group of the formula R.sup.8 --O-- wherein R.sup.8 is a protecting group for a hydroxyl group, a hydroxymethyl group, a formula group, a carboxyl group, a lower alkoxycarbonyl group, a lower alkanoyl group, an amino group, a mercapto group, or a group of the formula R.sup.6 --X--Y-- wherein R.sup.6 is a phenyl or thienyl group which may be 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, a furyl group, a tetrahydrofuryl group, a pyrrolyl group, pyrrolydinyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a furazanyl group, a thiazolyl group, an isothioazolyl group, a thiadiazolyl group, a thienyl group, a pyridyl group, a piperidyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a piperidinyl group, a morpholinyl group, a thiomorpholinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a benzofuranyl group, a benzothienyl group, a benzoisoxazolyl group, a benzothiazolyl group and a benzofurazanyl 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.sup.a -- wherein R.sup.a is a hydrogen atom or a lower alkyl group or a group of the formula --NR.sup.b -- wherein R.sup.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.sup.b -- wherein R.sup.b is as defined above, the other is a carbonyl group or a group of the formula --CHR.sup.a -- wherein R.sup.a is as defined above, and R.sup.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, comprising reacting a compound of the formula:
• ##STR19## wherein W is a halogen atom, R.sup.11 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 R.sup.21 is a hydrogen atom or a group of the formula:
• ##STR20## wherein R.sup.3, R.sup.4, R.sup.5, R.sup.31, R.sup.32, R.sup.41, R.sup.42 and R.sup.51 are as defined above, with an acetylene derivative of the formula:
• HC.tbd.C--R.sup.7 [V]
• wherein R.sup.7 is as defined above, in the presence of a palladium catalyst, to obtain a compound of the formula:
• ##STR21## wherein R.sup.11, R.sup.21 and R.sup.7 are as defined above, and, if necessary, N-alkylating this compound.