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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Visible-Light-Mediated alpha-Amino Alkylation of Azomethine Imines: An Approach to N-(beta-Aminoalkyl)pyrazolidinones

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Author(s):
Matsuo, Bianca T. [1] ; Correia, Jose Tiago M. [1] ; Paixao, Marcio W. [1]
Total Authors: 3
Affiliation:
[1] Fed Univ Sao Carlos UFSCar, Ctr Excellence Res Sustainable Chem CERSusChem, Dept Chem, BR-13565905 Sao Paulo - Brazil
Total Affiliations: 1
Document type: Journal article
Source: ORGANIC LETTERS; v. 22, n. 20, p. 7891-7896, OCT 16 2020.
Web of Science Citations: 0
Abstract

Herein, a mild and robust photocatalytic protocol for the combination of amino and pyrazolidinone functionalities through a radical alpha-amino alkylation of azomethine iminium ions is demonstrated. This method presents a high functional group tolerance providing direct access to a large family of N-(beta -aminoalkyl)pyrazolidinones in good to excellent yields, including the latestage incorporation of the pyrazolidinone moiety to pharmaceutical ingredients. We propose a plausible scenario for the C-C bond-forming step which involves radical addition followed by a spin-center-shift event. (AU)

FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Grantee:Arlene Gonçalves Corrêa
Support Opportunities: Research Grants - Research Centers in Engineering Program
FAPESP's process: 15/17141-1 - Development and Mechanism Studies of New Synthetic Methodologies for the Synthesis of Bioactive Compounds.
Grantee:Ricardo Samuel Schwab
Support Opportunities: Regular Research Grants
FAPESP's process: 18/12986-1 - Development of photochemical and electrocatalytic methodologies to the synthesis and modification of heterocyclic scaffolds
Grantee:Camila de Menezes Kisukuri
Support Opportunities: Scholarships in Brazil - Post-Doctoral
FAPESP's process: 17/10015-6 - Photocatalysis Applied to the Synthesis of N-heterocycles: New Strategies for Intercepting Radical Intermediates Generated in Processes Promoted by Visible-light-Tris (trimethylsilyl)silane Combination.
Grantee:José Tiago Menezes Correia
Support Opportunities: Scholarships in Brazil - Post-Doctoral