GB1325061A - Process for the production of azines - Google Patents

Abstract

1325061 Thiazolidine derivatives CIBAGEIGY AG 3 July 1970 32313/70 Heading C2C Novel compounds of Formula I (in which R is an allyl or 2-methylallyl group) are prepared by (a) heating a compound of Formula II or a salt of a tautomeric form of such a compound, with a reactive ester with regard to the hydroxyl group of glycolic acid, or (b) heating a compound of Formula IIa or a salt of a tautomeric form of such a compound, with a reactive ester with regard to the hydroxyl group of lactic acid. Starting materials of Formulae II and IIa are prepared by reacting a compound of Formula III (in which R 1 is CH 3 , allyl or 2-methylallyl and R 2 is H or C 1-5 alkyl) with a compound of Formula IV (in which Hal is Cl, Br or I, and R 3 is H when R 1 is CH 3 or R 3 is CH 3 when R 1 is allyl or 2- methylallyl) to give a compound of Formula V heating this compound in a C 1-5 alkanol in the presence of hydrogen chloride, or with hydrochloric acid, to give a hydrazone of Formula VI in the form of its hydrochloride, and reacting this compound, after conversion to the free base, with a compound of Formula VII: R 4 NCS (in which R 4 is CH 3 when R 3 is CH 3 , or R 4 is allyl or 2-methylallyl when R 3 is H). Compounds of Formula III are prepared by alkanoylation of 4-R 1 -substituted 3-thiosemicarbazides. Pharmaceutical compositions having tumourinhibiting activity, for oral, rectal or parenteral administration, comprise a compound of Formula I together with a pharmaceutical carrier. Reference has been directed by the Comptroller to Specification 1,122,604.