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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.)

Step economy strategy for the synthesis of amphoteric aminoaldehydes, key intermediates for reduced hydantoins

Full text
Author(s):
Monteiro, Julia L. [1] ; Moreira, Natalia M. [1] ; dos Santos, Deborah A. [1] ; Paixao, Marcio W. [1] ; Correa, Arlene G. [1]
Total Authors: 5
Affiliation:
[1] Univ Fed Sao Carlos, Ctr Excellence Res Sustainable Chem, BR-13565905 Sao Carlos, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: Pure and Applied Chemistry; v. 90, n. 1, p. 121-132, JAN 2018.
Web of Science Citations: 1
Abstract

Despite of the orthogonal reactivity of the N-H aziridines aldehyde, these compounds exist as an equilibrium of three different forms - whereas the dimeric one is mostly observed in a variety of solvents. In this work, we have developed an alternative protocol for the aminoaldehyde dimers synthesis in two steps starting with an organocatalyzed aziridination between alpha,beta-unsaturated aldehydes and a protected amine to afford known isolable and stable N-protected aziridine aldehydes. After Boc-deprotection, dimeric species were immediately formed from monomeric N-H aziridine aldehydes. From this building-block new reduced hydantoins were prepared via {[}3+2]-annulation with isocyanates. (AU)

FAPESP's process: 12/07284-1 - Asymmetric synthesis and biological evaluation of hydantoins and derivatives
Grantee:Júlia Lammoglia Monteiro
Support Opportunities: Scholarships in Brazil - Doctorate (Direct)
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: 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 - Applied Research Centers Program
FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
Grantee:Glaucius Oliva
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC