ONE-POT SYNTHESIS OF BENZOXAZINES FROM ANILINES AND EPOXIDES

• Grant number: 23/15846-4
• Support Opportunities: Scholarships in Brazil - Master
• Start date: March 01, 2024
• Status: Discontinued
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Claudio Francisco Tormena
• Grantee: Leonardo Claudio
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated scholarship(s): 24/22873-0 - REACTIVITY EFFECTS IN ONE-POT SYNTHESIS OF 1,4- DIHYDROBENZOXAZINES DERIVATIVES., BE.EP.MS

Abstract

The purpose of this research is to employ the one-pot methodology for the synthesis of benzoxazines through the combination of epoxides and anilines, aiming to compare the relationships between the contribution of stereoelectronic effects and the reaction kinetics of the total synthesis, while also serving as an alternative to the classical routes of obtaining these heterocycles through metal catalysis. In this regard, the following specific objectives have been established: a) Synthesize and characterize benzoxazine compounds through the combination of anilines and epoxides; b) monitoring the reaction kinetics profile of both classical and one-pot synthetic routes leading to the same product and perform theoretical calculations related to the electronic geometry of the transition state; and c) Evaluate new alternative one-pot synthetic routes for compounds of industrial and pharmacological interest. To achieve these objectives, the one-pot synthesis methodology for benzoxazines from anilines and epoxides will be applied, with quantitative analyses conducted using Nuclear Magnetic Resonance, and establishing relationships between the stereoelectronic effects of substituents in anilines and epoxides and their contributions to the overall process through the description and monitoring of the kinetic profile. The hypothesis of this research is based on the idea that the one-pot methodology allows for the obtainment of compounds with significantly higher overall reaction yield. It is expected to contribute to the field of organic synthesis through the optimization of experimental procedures.