Exploration of carbamoyl radical reactivity for the construction of quinolinones fused with gamma-lactones

• Grant number: 19/24784-7
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: February 01, 2020
• End date: January 31, 2021
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Leandro Helgueira de Andrade
• Grantee: Bianca Campanile Rocha
• Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

Given the important biological activity of heterocycles and their industrially and academic relevance, this project seeks to develop an efficient methodology for the synthesis of new highly substituted heterocycles. It is a cascade cyclization reaction of eninacrylamides with the carbamoyl radical for synthesis of ³-lactone fused quinolinones. It is intended to synthesize the substrate (N, 2-dimethyl-N- [2- (2- (phenylethynyl) phenyl)]-2-propenamide) and use it as a starting material for study with the carbamoyl radical, which is generated from formamide in light-excited medium and also can be generated within a redox system composed of Fe (II) and H2O2. This radical can be used to generate more substituted nucleus and is known for its reactivity with unsaturated systems. In the synthesis of fused quinolinones with ³-lactones five new bonds are formed and two new fused cycles are closed. This reaction sequence reveals a large structural variability that can be achieved with formamide chemistry, and reveals a new class of compounds that can be investigated for their reactivity and biological activity. (AU)

Scientific publications

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

SACCHELLI, BRUCE A. L.; ROCHA, BIANCA C.; ANDRADE, LEANDRO H.. Cascade Reactions Assisted by Microwave Irradiation: Ultrafast Construction of 2-Quinolinone-Fused gamma-Lactones from N-(o-Ethynylaryl)acrylamides and Formamide. ORGANIC LETTERS, v. 23, n. 13, p. 5071-5075, JUL 2 2021. (17/02854-8, 19/24784-7, 19/10762-1)