Regioselective synthetic approaches towards 1,2,8,9-tetraazadispiro[4.1.4.3]tetradeca-2,9-dien-6-ones

1,3-Dipolar cycloaddition of 2,6-bis(arylmethylidene)cyclohexanones 1 to a variety of nitrilimines (generated in situ by triethylamine dehydrohalogenation of the corresponding hydrazonoyl chlorides 2) proceeded regioselectively affording 1,3,4,8,10,11-hexaaryl-1,2,8,9-tetraazadispiro[4.1.4.3]tetradeca-2,9-dien-6-ones as a mixture of two isomers 3 and 4. The structures of which were established by different spectroscopic techniques as well as single crystal X-ray diffraction.