Synthesis of α-amino-1,3-dicarbonyl compounds via Ugi flow chemistry reaction: access to functionalized 1,2,3-triazoles.

Mol Divers

Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil.

Published: November 2017

The Ugi multicomponent reaction has been used as an important synthetic route to obtain compounds with potential biological activity. We present the rapid and efficient synthesis of [Formula: see text]-amino-1,3-dicarbonyl compounds in moderate to good yields via Ugi flow chemistry reactions performed with a continuous flow reactor. Such [Formula: see text]-amino-1,3-dicarbonyl compounds can act as precursors for the production of [Formula: see text]-amino acids via hydrolysis of the ethyl ester group as well as building blocks for the synthesis of novel compounds with the 1,2,3-triazole ring. The [Formula: see text]-amino acid derivatives of the Ugi flow chemistry reaction products were then used for dipeptide synthesis.

Download full-text PDF

Source
http://dx.doi.org/10.1007/s11030-017-9764-5DOI Listing

Publication Analysis

Top Keywords

ugi flow
12
flow chemistry
12
chemistry reaction
8
[formula text]-amino-13-dicarbonyl
8
text]-amino-13-dicarbonyl compounds
8
[formula text]-amino
8
compounds
5
synthesis
4
synthesis α-amino-13-dicarbonyl
4
α-amino-13-dicarbonyl compounds
4

Similar Publications

Visible Light Excitation of Poly-(para-Phenylene Ethynylene) Enables Heterogeneous Photocatalytic Oxidations of Amines in Flow.

Angew Chem Int Ed Engl

October 2024

Chimie Moléculaire, Macromoléculaire et Matériaux (C3M), UMR CNRS 7167, ESPCI Paris PSL, 10 rue Vauquelin, 75005, Paris, France.

Article Synopsis
  • Heterogeneous visible light photocatalysis offers a sustainable method for organic synthesis, but solid-state photocatalysts are often underused due to limited accessibility and unclear relationships between structure and function.
  • A new solid-state conjugated organic polymer, poly-(para-phenylene ethynylene), has been developed which demonstrates strong oxidative power when exposed to visible light, making it highly effective in transforming amines into imines.
  • The study reveals the polymer's superior photocatalytic activity through its fully conjugated structure, and showcases its potential in facilitating efficiently telescoped reactions for producing biologically important compounds.
View Article and Find Full Text PDF

Background: Non-variceal upper gastrointestinal bleeding (NVUGIB) is a common medical problem worldwide. Independent endoscopic risk factors for rebleeding and mortality of NVUGIB that are treatable are stigmata of recent hemorrhage (SRH) and arterial blood flow underneath SRH. The specific aims of this paper are to describe the importance of arterial blood flow detection for risk stratification and as a guide to definitive hemostasis of severe NVUGIB.

View Article and Find Full Text PDF

The combination of the Ugi reaction and electro-organic synthesis can aid in the creation of novel heterocycles that have not been previously explored. In this study, a new strategy utilizing bis-amides from the Ugi reaction has been developed, which can produce C-S, C-Se, and C-C═O functionalized five-membered spirolactams mediated by electricity under catalyst- and metal-free conditions. Notably, this approach can be applied using a microelectro-flow reactor (μ-EFR) for gram-scale synthesis.

View Article and Find Full Text PDF

PD-1 blockade attenuates surgery-mediated immunosuppression and boosts Th1 immunity perioperatively in oesophagogastric junctional adenocarcinoma.

Front Immunol

June 2023

Department of Surgery, Trinity St. James's Cancer Institute, Trinity Translational Medicine Institute, St. James's Hospital, Trinity College Dublin, Dublin, Ireland.

Introduction: This timely study assesses the immunosuppressive effects of surgery on cytotoxic Th1-like immunity and investigates if immune checkpoint blockade (ICB) can boost Th1-like immunity in the perioperative window in upper gastrointestinal cancer (UGI) patients.

Methods: PBMCs were isolated from 11 UGI patients undergoing tumour resection on post-operative days (POD) 0, 1, 7 and 42 and expanded using anti-CD3/28 and IL-2 for 5 days in the absence/presence of nivolumab or ipilimumab. T cells were subsequently immunophenotyped flow cytometry to determine the frequency of T helper (Th)1-like, Th1/17-like, Th17-like and regulatory T cell (Tregs) subsets and their immune checkpoint expression profile.

View Article and Find Full Text PDF

Purpose: The purpose of this study was to describe the optical coherence tomography (OCT) angiography findings as a predictive role in the chronic relapsing stage of Vogt-Koyanagi-Harada disease and its comparison with other imaging modalities such as fluorescein angiography, indocyanine-green angiography, and spectral domain OCT.

Methods: A 37-year-old woman from Bangladesh was diagnosed with Vogt-Koyanagi-Harada disease. She was evaluated 8 months before for a routine examination when she was in clinical remission.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!