RESUMEN
A highly efficient, catalyst-free, metal-free, atom economical green protocol for the synthesis of arylthio/arylamino methylene compounds by a Michael attack of arylthiols and anilines on nitroolefins derived from acenaphthaquinone and isatin has been developed. The method needs methanol as a reaction solvent and does not require any recrystallization, work-up process or column chromatography. (E)-Arylthio alkenes and (Z)-arylamino alkenes were obtained as the sole products. The results obtained from computational studies using density functional theory on ORCA program (B3LYP/def2-SVP level) are in good agreement with the data obtained from the single crystal X-ray analysis.
RESUMEN
Reactions of 3-benzylidene succinimides with 2-substituted 2-hydroxy-indane-1,3-diones and unsaturated pyrazolones are carried out under basic conditions to afford spirocyclized derivatives and Michael adducts, respectively, with high regio- and stereo-selectivities. The most notable aspect of the reaction is the ability of highly reactive benzylidene succinimide to act as both an electrophile and a nucleophile causing spirocyclization. The reaction proceeded under mild and metal-free conditions and products were isolated in good to high yields. The current strategy utilizes simple and easily accessible precursors, and provides functionally rich products of medicinal interest with two to four contiguous stereogenic centres and complete regioselectivity with excellent diastereoselectivity.