Highly Regioselective 1,3-Dipolar Cycloaddition of Nitrilimines and Thioaurones Towards Spiro-2-Pyrazolines: Synthesis, Characterization, and Mechanistic Study
Mohamed Bakhouch,
Bouchra Es-Sounni,
Ayoub Ouaddi,
Khaoula Oudghiri,
Mohammed Chalkha,
Lahoucine Bahsis,
Taoufiq Benali,
Mohamed Bourass,
Rabiaa Fdil,
Mohamed Akhazzane,
Mohamed El Yazidi
Affiliations
Mohamed Bakhouch
Bioorganic Chemistry Team, Department of Chemistry, Faculty of Sciences, Chouaïb Doukkali University, El Jadida 24000, Morocco
Bouchra Es-Sounni
Bioorganic Chemistry Team, Department of Chemistry, Faculty of Sciences, Chouaïb Doukkali University, El Jadida 24000, Morocco
Ayoub Ouaddi
Bioorganic Chemistry Team, Department of Chemistry, Faculty of Sciences, Chouaïb Doukkali University, El Jadida 24000, Morocco
Khaoula Oudghiri
Laboratoire de Recherche en Développement Durable et Santé, Faculté des Sciences et Techniques de Marrakech, Université Cadi Ayyad, Marrakech 40000, Morocco
Mohammed Chalkha
Laboratory of Materials Engineering for the Environment and Natural Resources, Faculty of Sciences and Techniques, University of Moulay Ismail of Meknes, B.P 509, Boutalamine, Errachidia 52000, Morocco
Lahoucine Bahsis
Laboratoire de Chimie Analytique et Moléculaire, LCAM, Faculté Poly disciplinaire de Safi, Université Cadi Ayyad, Safi 4162, Morocco
Taoufiq Benali
Environment and Health Team, Polydisciplinary Faculty of Safi, Cadi Ayyad University, Safi 46030, Morocco
Mohamed Bourass
Laboratoire de Physicochimie des Polymères et des Interfaces (LPPI), Cy Cergy Paris Université, 5 Mail Gay CEDEX, 95031 Cergy-Pontoise, France
Rabiaa Fdil
Bioorganic Chemistry Team, Department of Chemistry, Faculty of Sciences, Chouaïb Doukkali University, El Jadida 24000, Morocco
Mohamed Akhazzane
Engineering Laboratory of Organometallic, Molecular Materials and Environment, Faculty of Sciences Dhar EL Mahraz, University Sidi Mohamed Ben Abdellah, P.O. Box 1796, Fez 30000, Morocco
Mohamed El Yazidi
Engineering Laboratory of Organometallic, Molecular Materials and Environment, Faculty of Sciences Dhar EL Mahraz, University Sidi Mohamed Ben Abdellah, P.O. Box 1796, Fez 30000, Morocco
In this paper, we report a highly regioselective 1,3-dipolar cycloaddition (1,3-DC) reaction of nitrilimines with thioaurone derivatives that afforded the hitherto unreported spiropyrazolines. Spectroscopic and spectrometric data were utilized to confirm the structure of all products and elucidate the reaction’s regiochemistry. A mechanistic study was performed within the Molecular Electron Density Theory (MEDT) at the B3LYP/6-311G(d,p) computational level to explain the regioselectivity observed. The electron localization function (ELF) topological analysis confirms the carbenoid-type (cb-type) mechanism of the cycloaddition reactions between nitrilimines and thioaurones. The intermolecular interactions between reagents in this reaction account for the regioselectivity observed experimentally.
