Synthesis of 2-(chloro(methoxy, morpholino)methyl)-hexahydropyrimidothieno[3,2-c]azocines and tetrahydrospiro[pyrido[4,5']thieno[2,3-d]pyrimidines]

2-(Chloromethyl)-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4(3H)-ones reacted with acetylenedicarboxylate ester, methyl propiolate or acetylacetylene, forming mixtures of 2-(chloromethyl)-5,6,7,10-tetrahydropyrimido[5',4':4,5]thieno[3,2-d]azocin-4(3H)-ones and 2'-chloromethyl-6'-methylidene-2,3-dihydro-1H-spiro[pyrido[4,5']thieno[2,3-d]pyrimidin]-4'(3'H)-ones in various ratios. Analogous products were also obtained in the reaction of 2-(methoxymethyl) derivative with methyl propiolate, while using 2-[(morpholin-4-yl)-methyl] derivative in a similar reaction led to the formation of a more complex product mixture. © 2015 Springer Science+Business Media New York.