REACTIVITY EFFECTS IN ONE-POT SYNTHESIS OF 1,4- DIHYDROBENZOXAZINES DERIVATIVES.

• Grant number: 24/22873-0
• Support Opportunities: Scholarships abroad - Research Internship - Master's degree
• Start date: March 30, 2025
• End date: July 29, 2025
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Claudio Francisco Tormena
• Grantee: Leonardo Claudio
• Supervisor: Bruno Linclau
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Institution abroad: Ghent University (UGent), Belgium
• Associated to the scholarship: 23/15846-4 - ONE-POT SYNTHESIS OF BENZOXAZINES FROM ANILINES AND EPOXIDES, BP.MS

Abstract

Substitution reactions on aromatic rings, such as electrophilic (SEAr) and nucleophilic (SNAr) substitutions, have been widely studied due to their significant synthetic importance. Findings indicate that Meisenheimer intermediates in SNAr reactions are sometimes energetically too unstable, suggesting that in these cases a one-step, non-concerted mechanism would prevail, in which the C-F bond formation precedes C-O bond cleavage. Based on preliminary data involving a one-pot methodology for the synthesis of 1,4-dihydrobenzoxazine derivatives, which involves an intramolecular SNAr substitution reaction, the substitution pattern is unfavourable for Meisenheimer intermediates to occur. This BEPE project aims to investigate the relationship between the substituents in the phenyl ring and the observed reactivity.