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The ketene aminals  9a–e  can be prepared from the orthoamide of propiolic acid  6a  and 2-methyl-5-phenacyl-1,3,4-thiadiazoles  8a–e  under mild conditions. The crystal structure analyses of  9b  and  9d  reveal that compounds  9  can be regarded as 1,4-dipoles (push-pull-substituted butadienes). Surprisingly, the analogous reactions of the orthoamides  6b , c  with the thiadiazoles  8a–c  give rise to the formation of 1,2-dihydro-pyridin-2-thiones  13a–j . The constitution of the compounds  13  was confirmed by crystal structure analyses of the compounds  13c , f , g , i .

Orthoamide und Iminiumsalze, XCIV a . Kondensationsreaktion von Orthoamiden von Alkincarbonsäuren mit 2-Methyl-5-phenacyl-1,3,4-thiadiazolen