4.4 Article

Multicomponent Mannich reactions: General aspects, methodologies and applications

期刊

TETRAHEDRON
卷 73, 期 50, 页码 6977-7004

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2017.10.063

关键词

Multicomponent Mannich reactions; Catalysts; Ionic liquids; Naphthoquinones

资金

  1. Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq) [303464/2015-1, 448886/2014-6]
  2. Coordenadoria de Aperfeicoamento de Pessoal do Nivel Superior (CAPES)
  3. Fundacao de Amparo a Pesquisa do Espirito Santo (FAPES) [54684722/2011]

向作者/读者索取更多资源

The multicomponent Mannich reaction is a green and classical method for the preparation of beta-aminoketones and beta-aminoaldehydes (Mannich bases) and, as such, is one of the most important reactions in organic chemistry. The resulting Mannich bases are of particular interest due to their biological activity as well as their use as synthetic building blocks and precursors of valuable pharmaceuticals products. In this context, various elegant methods for multicomponent Mannich reactions have been developing over last years. This review updates these reactions, including naphthoquinone derivatives that possess varied and important biological activities and whose Mannich reaction has been little explored in the literature. (C) 2017 Elsevier Ltd. All rights reserved.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.4
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

Review Chemistry, Organic

para-Quinone Methides as Acceptors in 1,6-Nucleophilic Conjugate Addition Reactions for the Synthesis of Structurally Diverse Molecules

Carolina G. S. Lima, Fernanda P. Pauli, Dora C. S. Costa, Acacio S. de Souza, Luana S. M. Forezi, Vitor F. Ferreira, Fernando de Silva da Silva

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Biochemical Research Methods

Fiber spray ionization mass spectrometry in forensic chemistry: A screening of drugs of abuse and direct determination of cocaine in urine

Joao Francisco Filho Allochio, Nayara A. dos Santos, Keyller Bastos Borges, Valdemar Lacerda, Fabricio Souza Pelicao, Wanderson Romao

RAPID COMMUNICATIONS IN MASS SPECTROMETRY (2020)

Review Chemistry, Medicinal

Biological activities of [1,2,4]triazolo[1,5-a]pyrimidines and analogs

Sergio Pinheiro, Erick M. C. Pinheiro, Estela M. F. Muri, Jaqueline C. Pessoa, Mayara A. Cadorini, Sandro J. Greco

MEDICINAL CHEMISTRY RESEARCH (2020)

Article Chemistry, Medicinal

2H-1,2,3-Triazole-chalcones as novel cytotoxic agents against prostate cancer

Sergio Pinheiro, Jaqueline C. Pessoa, Erick M. C. Pinheiro, Estela M. F. Muri, Eclair Venturini Filho, Laiza B. Loureiro, Maria Clara R. Freitas, Carlos M. D. Silva Junior, Rodolfo G. Fiorot, Jose Walkimar M. Carneiro, Karina M. Rotamiro, Anderson R. A. Guimaraes, Karin J. P. Rocha-Brito, Sandro J. Greco

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2020)

Review Biochemical Research Methods

Molecularly imprinted polymers as a selective sorbent for forensic applications in biological samples-a review

Juliana Barreto Ferreira, Clebson de Jesus Macrino, Laise Aparecida Fonseca Dinali, Joao Francisco Allochio Filho, Camilla Fonseca Silva, Keyller Bastos Borges, Wanderson Romao

Summary: Molecularly imprinted polymers (MIP) are a molecular recognition technology with applicability in various fields, including forensic chemistry. In the forensic context, MIP has been increasingly used in the analysis of biological fluids, particularly in the preparation of samples for the analysis of stimulant drugs.

ANALYTICAL AND BIOANALYTICAL CHEMISTRY (2021)

Article Energy & Fuels

Study of Thermal Aging of Model Compounds Present in Asphalt Cement by GC/MS, ESI-MS, NMR, and FTIR

Nata C. L. Madeira, Polianna da S. Ferreira, Joao F. Allochio Filho, Luiz S. Chinelatto Jr, Margareth C. C. Cravo, Adriana T. Martins, Valdemar Lacerda Jr, Wanderson Romao

Summary: The study investigates the chemical variations in petroleum asphalt cement aging, using 15 standards of model compounds to represent different fractions. Results show an increase in degradation as temperature rises, including oxidation, polymerization, and formation of double bonds as observed reactions.

ENERGY & FUELS (2021)

Article Chemistry, Organic

Aminopyrimidines: Recent synthetic procedures and anticancer activities

Eclair Venturini Filho, Erick M. C. Pinheiro, Sergio Pinheiro, Sandro J. Greco

Summary: This review discusses the strategies and methods for developing aminopyrimidine derivatives, including optimization of synthetic protocols and implementation of multicomponent reactions. It also covers the use of these derivatives as anticancer agents and their main activities in cancer treatment.

TETRAHEDRON (2021)

Article Chemistry, Medicinal

Synthetic enamine naphthoquinone derived from lawsone as cytotoxic agents assessed by in vitro and in silico evaluations

Barbara C. Lemos, Regina Westphal, Eclair Venturini Filho, Rodolfo G. Fiorot, Jose Walkimar M. Carneiro, Anne Caroline C. Gomes, Celina J. Guimaraes, Fatima C. E. de Oliveira, Pedro Mikael S. Costa, Claudia Pessoa, Sandro J. Greco

Summary: Ten enamine naphthoquinones were synthesized with yields ranging from 43 to 76%, and were screened for antiproliferative activities against human cancer cell lines. Compounds bearing picolylamine and quinoline moieties showed the highest activities, potentially acting as anticancer molecules by inhibiting topoisomerase-II and thymidylate synthase, as suggested by in silico evaluations and Molecular Docking simulations.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS (2021)

Review Chemistry, Organic

Enantioselective Povarov Reactions: An Update of a Powerful Catalytic Synthetic Methodology

Barbara C. Lemos, Eclair Venturini Filho, Rodolfo G. Fiorot, Fabrizio Medici, Sandro J. Greco, Maurizio Benaglia

Summary: This MiniReview compiles the most significant successful examples of highly efficient enantioselective catalytic protocols for the Povarov reaction since 2014, and provides a comprehensive discussion of different catalytic strategies employed in recent years. It also critically discusses the controversial dispute regarding the mechanistic pathways of this well-known reaction.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Physics, Atomic, Molecular & Chemical

Paper spray ionization coupled to Fourier Transform Ion Cyclotron Resonance Mass Spectrometry as a tool to fight the counterfeiting of medicines

Maira Kerpel dos Santos, Nayara Araujo dos Santos, Joao Francisco Allochio Filho, Layla Paixao Santos, Wanderson Romao, Rafael Scorsatto Ortiz

Summary: The study utilized Paper Spray Ionization (PSI) coupled to Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FT-ICR MS) to chemically profile 92 samples of counterfeit medicines and ecstasy tablets. Different strategies for medicine counterfeiting and cross contamination with other substances were identified, providing important evidence for police intelligence.

INTERNATIONAL JOURNAL OF MASS SPECTROMETRY (2021)

Article Chemistry, Multidisciplinary

Tandem Synthesis of Furanaphthoquinones via Enamines and Evaluation of Their Antiparasitic Effects against Trypanosoma cruzi

Mariana F. C. Cardoso, Luana S. M. Forezi, Acacio S. de Souza, Ana F. M. Faria, Raissa M. S. Galvao, Murilo L. Bello, Fernando C. da Silva, Robson X. Faria, Vitor F. Ferreira

Summary: Furanaphthoquinones are synthesized through a tandem reaction between lawsone and cyclic ketones, providing a method for synthesizing compounds with activity against T. cruzi. Compound 9b shows high potency in killing the parasite, reduced toxicity towards mammalian cells, and acts on CYP51. Candidate 9b demonstrates the best profile when bound to CYP51.

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY (2022)

Article Chemistry, Organic

A Green Multicomponent Domino Mannich-Michael Reaction to Synthesize Novel Naphthoquinone-Polyphenols with Antiproliferative and Antioxidant Activities

Eclair Venturini Filho, Mariana K. Antoniazi, Rafael Q. Ferreira, Gabriel F. S. dos Santos, Claudia Pessoa, Celina J. Guimaraes, Jose B. Vieira Neto, Artur M. S. Silva, Sandro J. Greco

Summary: This study presents a new green synthesis method for naphthoquinone-polyphenols and successfully synthesizes twelve novel compounds with good antiproliferative activity and antioxidant capacity under optimized conditions.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2022)

Article Biochemistry & Molecular Biology

Green Synthesis of Spiro Compounds with Potential Anticancer Activity through Knoevenagel/Michael/Cyclization Multicomponent Domino Reactions Organocatalyzed by Ionic Liquid and Microwave-Assisted

Regina Westphal, Eclair Venturini Filho, Laiza Bruzadelle Loureiro, Claudio Francisco Tormena, Claudia Pessoa, Celina de Jesus Guimaraes, Mariana Palmeira Manso, Rodolfo Goetze Fiorot, Vinicius Rangel Campos, Jackson Antonio Lamounier Camargos Resende, Fabrizio Medici, Sandro Jose Greco

Summary: In this study, a microwave-assisted Knoevenagel/Michael/cyclization multicomponent domino methodology was developed for the synthesis of spiro compounds. Twelve spiro compounds were synthesized and one of them exhibited anti-cancer activity.

MOLECULES (2022)

Article Chemistry, Inorganic & Nuclear

Spin-frustration with two quasi-degenerated spin states of a copper(II) heptanuclear complex obtained from an amino acid ligand

Catiucia R. M. O. Matos, Henrique C. S. Junior, Dayenny L. D'Amato, Acacio S. de Souza, Sergio Pinheiro, Guilherme P. Guedes, Glaucio B. Ferreira, Odivaldo C. Alves, Filipe B. de Almeida, Flavio Garcia, Celia M. Ronconi

DALTON TRANSACTIONS (2020)

Article Chemistry, Analytical

Development, validation and evaluation of a quantitative method for the analysis of twenty-four new psychoactive substances in oral fluid by LC-MS/MS

Travon Cooman, Heloa Santos, Joseph Cox, Joao Francisco Allochio Filho, Keyller Bastos Borges, Wanderson Romao, Luis E. Arroyo-Mora

FORENSIC CHEMISTRY (2020)

Article Chemistry, Organic

Facile synthesis of quinoxaline catalyzed by iron-based carbon material in water

Fuying Zhu, Yamei Lin

Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.

TETRAHEDRON (2024)

Article Chemistry, Organic

Simple approach towards phosphorus-substituted spiro 1,3,4-thiadiazolines

Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova

Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.

TETRAHEDRON (2024)

Article Chemistry, Organic

Recent advances in the synthesis of 2-cyclopentenones

Jisna Jose, Thomas Mathew

Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.

TETRAHEDRON (2024)