Fast Transition Metal-Free Synthesis of Functionalized Oxindoles and Dihydroquinoline-2-ones Under Microwave Irradiation

Author(s)

Couto, Julia L. ; Hornink, Milene M. ; Nascimento, Vinicius R. ; Andrade, Leandro H.

• Document type: Journal article
• Source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY; v. 2022, n. 44, p. 10-pg., 2022-11-25.

Abstract

A fast transition metal-free and synthetic methodology for generating a broad scope of highly functionalized oxindoles and dihydroquinolin-2-ones was developed. The exploitation of formamide or N-methylformamide (reagent/solvent) and potassium persulfate (radical initiator) under microwave irradiation resulted in a fast radical reaction of 10 s. The functionalized oxindoles and dihydroquinoline-2-ones allowed us to readily access several spirocompounds such as spiro[oxindole-gamma-lactones], spiro[oxindole-delta-lactones], spiro[dihydroquinoline-2-one-gamma-lactones], spiro[oxindole-imides] and spiro[dihydroquinoline-2-one-imides]. (AU)

• FAPESP's process: 18/07152-4 - Application of vanadium-dependent haloperoxidase in a continuous flow system aiming selective reactions
• Grantee: Milene Macedo Hornink
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
• FAPESP's process: 21/12555-3 - Exploitation of formamide reactivity as an alternative pathway of CO2 incorporation to produce renewable polymers
• Grantee: Leandro Helgueira de Andrade
• Support Opportunities: Regular Research Grants
• FAPESP's process: 19/10762-1 - Development of a synthetic platform using carbamoyl radicals: application of the formamide in the synthesis of heterocyclic compounds
• Grantee: Leandro Helgueira de Andrade
• Support Opportunities: Regular Research Grants
• FAPESP's process: 17/02854-8 - Synthetic applications of carbamoyl radicals via photocatalysis
• Grantee: Leandro Helgueira de Andrade
• Support Opportunities: Regular Research Grants