AN EXHAUSTIVE COMPUTATIONAL MECHANISTIC STUDY OF THE GOULD?JACOBS TYPE THERMAL CYCLIZATION USING COUPLED CLUSTERS AND DFT FIRST PRINCIPLES METHODOLOGIES

MALVACIO, IVANA; ELIZABETH L. MOYANO; D. MARIANO VERA

VILLA CARLOS PAZ - CORDOBA

Conferencia; 13rd Latin American Conference on Physical Organic Chemistry (CLAFQO-13); 2015

Facultad de Cs. Quimicas - UNC

The quinolone structure has been extensively used in a variety of pharmacologically active compounds as antibacterial, anticancer and antimalarial3 among others. Since its first application in 1939, the Gould-Jacobs (G-J) reaction became one of the most common used strategies to synthesize quinolones. However, to the best of our knowledge, this complex multistep mechanism has never been study in-depth.Here we report a thorough computational mechanistic study of the G-J reaction performed using DFT and ab-initio (Coupled-Cluster) methods. The reaction between anilines (1) and diethylethoxymethylenmalonate(2) under microwave (MW) irradiation combined with Flash VacuumPyrolysis (FVP) was considered as a case study.