In a multistep reaction, indeno[2,1- e][1,3,4]oxadiazine-9-one, oxoindeno[1,2- c]- pyrazolecarbothioamide, (thioxo-1,2,4-triazaspiro[4.5]decadienylidene)malononitrile and spiro-(fluorine-9,3′-[1,2,4]triazoline)-5′-thione derivatives have been formed from a series of (substituted ylidene)- N-phenylhydrazinecarbothioamides 1a–e with (1,3-dioxo-2,3-dihydro-1 H-inden-2-ylidene)propanedinitrile, 7,7′,8,8′-tetracyanoquinodimethane and (2,4,7-trinitro-9 H-fluoren-9-ylidene)propanedinitrile in aerated pyridine. Rationales of these conversions involving the nucleophilic reactions, condensation, dehydrogenation and oxidation are presented.