A theoretical analysis of the reactivity of acyl derivatives of azaheterocycles as dienophiles in cycloaddition reactions

KNEETEMAN, MARÍA N.; MANCINI, PEDRO M. E.; ORMACHEA, CARLA M.

Basel

Conferencia; The 21st International Electronic Conference on Synthetic Organic Chemistry; 2017

A theoretical study of the behavior of N-tosylacylpyrroles and N-tosylacylindoles being electrophilic dienophiles in polar Diels-Alder reactions is developed. Their reactivity is evaluated joint to different nucleophilic dienes. Calculations were developed considering the experimental results of these reactions in thermal conditions. The computational theoretical methods employed are based in the Density Functional Theory. It was observed that the acyl pentaheterocycles suffer the cycloaddition yielding indol derivatives and the benzofused ones convert into carbazole derivatives trough a concerted and asynchronous cycloaddition mechanism. The stereochemistry is defined by the acyl group in the dienophile and the substituent groups of the dienes.