Regioselective and stereoselective synthesis of epithiomethanoiminoindeno[1,2-b]furan-3-carbonitrile: heterocyclic [3.3.3]propellanes

Synthesis of heteropropellanes in one step: the reaction between dicyanomethylene-1,3-indanedione (CNIND) and N -substituted-2-(2,4-dinitrophenyl)hydrazinecarbothioamides, furnished (3a R ,8b S , Z )-2-amino-9-substituted-10-(2-(2,4-dinitrophenyl)hydrazono)-4-oxo-4 H -3a,8b-(epithiomethanoimino)indeno[1,2-b]furan-3-carbonitrile as a type of (2,4-dinitrophenyl)hydrazono[3.3.3]propellanes in good yields as single diastereomers. Structure determination and confirmation of the synthesized products have been achieved using various and modern spectroscopic techniques such as IR, NMR ( 1 H NMR and 13 C NMR), mass spectrometry, as well as X-ray crystal analysis. The X-ray structure data cleared that the molecule of 7a was crystalized as monoclinic, space group C2/c (no.15). Graphic abstract