Development of a synthetic platform using carbamoyl radicals: application of the formamide in the synthesis of heterocyclic compounds

• Grant number: 19/10762-1
• Support Opportunities: Regular Research Grants
• Start date: August 01, 2019
• End date: July 31, 2021
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Leandro Helgueira de Andrade
• Grantee: Leandro Helgueira de Andrade
• Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

Formamide is an organic compound mainly used as solvent in several industrial applications. Due to its wide application, large quantities and low price are commercial available. Recently, we have shown for the first time that carbamoyl radicals prepared from formamides can be applied to synthetize important heterocyclic compounds. Considering the relevance of different classes of heterocyclic compounds, the present research proposal has as main goal to expand the methodology that makes use of carbamoyl radicals for the preparation of different synthetic targets. For this purpose, we intend to explore the reactivity of the carbon-centered radical of formamide with different unsaturated esters or amides. In addition, the reactivity of the nitrogen atom of formamide can also be exploited in cyclization reactions. It is expected that novel heterocyclic compounds will be synthesized in few steps, and under continuous flow conditions. (AU)

Scientific publications

(8)

(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)

SANZ, CAROLINE G.; DIAS, KEVIN A.; BACIL, RAPHAEL P.; SERAFIM, RICARDO A. M.; ANDRADE, LEANDRO H.; FERREIRA, I, ELIZABETH; SERRANO, SILVIA H. P.. Electrochemical characterization of para- and meta-nitro substituents in aqueous media of new antichagasic pharmaceutical leaders. Electrochimica Acta, v. 368, FEB 1 2021. (17/02854-8, 19/10762-1)

COUTO, JULIA L.; HORNINK, MILENE M.; NASCIMENTO, VINICIUS R.; ANDRADE, LEANDRO H.. Fast Transition Metal-Free Synthesis of Functionalized Oxindoles and Dihydroquinoline-2-ones Under Microwave Irradiation. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2022, n. 44, p. 10-pg., 2022-11-25. (18/07152-4, 21/12555-3, 19/10762-1, 17/02854-8)

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)

SANABRIA, MARIALY NIEVES; ANDRADE, LEANDRO HELGUEIRA. Microwave Irradiation and Formamide: A Perfect Match for Ultrafast Carbamoylation via Radical Reactions. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, v. 9, n. 41, p. 13735-13741, OCT 18 2021. (19/10762-1)

HORNINK, MILENE M.; NASCIMENTO, VINICIUS R.; COUTO, JULIA L.; SANTOS, CAROLINE S.; ANDRADE, LEANDRO H.. Ultrasound-mediated radical cascade reactions: Fast synthesis of functionalized indolines from 2-(((N-aryl)amino)methyl)acrylates. ULTRASONICS SONOCHEMISTRY, v. 79, NOV 2021. (18/07152-4, 14/50316-7, 19/10762-1)

NASCIMENTO, VINICIUS R.; SUENAGA, MELISSA L. S.; ANDRADE, LEANDRO H.. An efficient approach for the synthesis of new (+/-)-coixspirolactams. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 18, n. 28, p. 5458-5465, JUL 28 2020. (19/10762-1, 17/02854-8)

HORNINK, MILENE MACEDO; LOPES, ALICE UVA; ANDRADE, LEANDRO HELGUEIRA. Biobased Spiroimides from Itaconic Acid and Formamides: Molecular Targets for a Novel Synthetic Application of Renewable Chemicals. SYNTHESIS-STUTTGART, v. 53, n. 02, p. 296-308, JAN 19 2021. (18/07152-4, 19/10762-1, 17/02854-8)

SANABRIA, MARIALY N.; HORNINK, MILENE M.; CORREIA, VALQUIRIA G.; ANDRADE, LEANDRO H.. Nontraditional Application of the Photo-Fenton Process: A Novel Strategy for Molecular Construction Using Formamide and Flow Chemistry. ORGANIC PROCESS RESEARCH & DEVELOPMENT, v. 24, n. 10, p. 2288-2297, OCT 16 2020. (19/10762-1, 17/02854-8)