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Application of Multicomponent Reactions in the Total Synthesis of Natural Peptides
The Free Internet Journal Review for Organic Chemistry Archive for Arkivoc 2019, part i, 0-0 Organic Chemistry to be inserted by editorial office Application of multicomponent reactions in the total synthesis of natural peptides Ghodsi Mohammadi Ziarani,* Razieh Moradi, and Leyla Mahammadkhani Department of Chemistry, Alzahra University, Vanak Square, P.O. Box 1993893973, Tehran, Iran E-mail address: [email protected], [email protected] Received 10-10-2018 Accepted 03-01-2019 Published on line 04-28-2019 Dates to be inserted by editorial office Abstract Multicomponent reactions (MCRs) have been widely applied for the synthesis of biologically active molecules with high complexity and diversity. Nowadays, total synthesis of natural peptides, due to their multifarious application areas, has attracted much attention of organic chemists. MCRs are a powerful and efficient method for the production of natural peptides in a limited number of steps. This review presents an overview on application of multicomponent reactions as a key step in the synthesis of natural peptides. Keywords: Natural peptides, natural products, multicomponent reactions, biological activity DOI: https://doi.org/10.24820/ark.5550190.p010.779 Page 1 ©ARKAT USA, Inc Arkivoc 2019, i, 0-0 Mohammadi-Ziarani, G. et al. Table of Contents 1. Introduction 2. Application of Multicomponent Reactions in the Total Synthesis of Natural Peptides 2.1. Syntheses based on the Ugi reaction 2.2. Syntheses based on the Passerini reaction 2.3. Miscellaneous reactions 3. Conclusions -
Ugi Four-Component Reaction (U-4CR) Under Green Conditions Designed for Undergraduate Organic Chemistry Laboratories
World Journal of Chemical Education, 2017, Vol. 5, No. 5, 153-157 Available online at http://pubs.sciepub.com/wjce/5/5/2 ©Science and Education Publishing DOI:10.12691/wjce-5-5-2 Ugi Four-component Reaction (U-4CR) Under Green Conditions Designed for Undergraduate Organic Chemistry Laboratories Mariana Ingold, Lucia Colella, Rosina Dapueto, Gloria. V. López*, Williams Porcal* Department of Organic Chemistry, Faculty of Chemistry, University of the Republic, Montevideo, Uruguay *Corresponding author Abstract Multicomponent reactions (MCRs) are a green strategy in which a collection of molecules with a great diversity are generated with a minimum of synthetic effort, time and by-products formation. The Ugi Multi-component reaction is a chemical reaction in which an aldehyde, an amine, a carboxylic acid and an isocyanide react to form a α-bisamide. In this work, we use the Ugi reaction, as an example of MCRs, to approach organic chemistry undergraduate students to sustainable reactions. This reaction can be carried out under on-water or solvent-free conditions, both at room temperature as in combination with microwave irradiation or ultrasound. The advantages and limitations of the usage of Ugi reaction, under these conditions, in an organic chemistry laboratory course are discussed. In this context, we used different parameters to calculate how environmentally friendly the assayed conditions are. The Chemical Manufacturing Methods for the 21st Century Pharmaceutical Industries (CHEM21 project) were used with this objective. The present work could contribute to the teaching of ecofriendly synthetic strategies, demonstrating the scientific and academic benefits of green chemistry. Keywords: green chemistry, solvent-free, on-water, microwave, Multicomponent Reaction, Ugi, Metrics Toolkit Cite This Article: Mariana Ingold, Lucia Colella, Rosina Dapueto, Gloria. -
Synthesis and Biological Importance of Amide Analogues
REVIEW ARTICLE Synthesis and biological importance of amide analogues Preeti Rajput, Abhilekha Sharma* Rajput P, Sharma A. Synthesis and biological importance of amide amide linage containing compounds. The main purpose of article is to analogues. J Pharmacol Med Chem 2018;2(1):22-31. provide information on the development of novel amide derivatives to the scientific community. Doing so, it focuses on mechanisms of action and ABSTRACT adverse events, and suggests measures to be implemented in the clinical The present research article deals with the amide analogues prepared by practice according to bioethical principles. available very well-known name reactions. The author have studied the name reactions like Beckmann rearrangement, Schmidt reaction, Passerine reaction, Key Words: Novel amide derivatives; Amide analogues; Amide formation Willgerodt–Kindler reaction and UGI reaction, which involves preparation of routes starting from substrates other than carboxylic acids and their T he Amide bond formation reactions are among the most important derivatives (5). Thus, with the help of transition metals, a plethora of transformations in organic chemistry and biochemistry because of the functional groups, such as nitriles, aldehydes, ketones, oximes, primary widespread occurrence of amides in pharmaceuticals, natural products alcohols or amines, can be now conveniently employed as starting and biologically active compounds. The amide group is widely present in materials for the construction of the amide bond. There are three types of the drugs, intermediates, pharmaceuticals, and natural products. It is also amides available in Chemistry: (i) an organic amide which is also referred available in large number of industrial materials including polymers, as carboxamide, (ii) a sulfonamide, and (iii) a phosphoramide. -
Investigating Ugi/Passerini Multicomponent Reactions for the Site-Selective Conjugation of Native Trastuzumab C
Investigating Ugi/Passerini Multicomponent Reactions for the Site-Selective Conjugation of Native Trastuzumab C. Sornay, S. Hessmann, S. Erb, I. Dovgan, A. Ehkirch, T. Botzanowski, S. Cianferani, A. Wagner, G. Chaubet To cite this version: C. Sornay, S. Hessmann, S. Erb, I. Dovgan, A. Ehkirch, et al.. Investigating Ugi/Passerini Mul- ticomponent Reactions for the Site-Selective Conjugation of Native Trastuzumab. Chemistry - A European Journal, Wiley-VCH Verlag, 2020, 26 (61), pp.13797-13805. 10.1002/chem.202002432. hal-02966878 HAL Id: hal-02966878 https://hal.archives-ouvertes.fr/hal-02966878 Submitted on 13 Nov 2020 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Investigating Ugi / Passerini multicomponent reactions for the Site-Selective Conjugation of Native Trastuzumab Charlotte Sornay1, Steve Hessmann2, Stéphane Erb2, Igor Dovgan1, Anthony Ehkirch2, Thomas Botzanowski2, Sarah Cianférani2, Alain Wagner1, Guilhem Chaubet1* AUTHOR ADDRESS 1Bio-Functional Chemistry (UMR 7199), LabEx Medalis, University of Strasbourg, 74 Route du Rhin, 67400 Illkirch-Graffenstaden, France 2Laboratoire de Spectrométrie de Masse BioOrganique (LSMBO), LabEx Medalis, Université de Strasbourg, CNRS, IPHC UMR 7178, 67000 Strasbourg, France KEYWORDS Bioconjugation; multicomponent reaction; antibodies; antibody-drug conjugates ABSTRACT: Site-selective modification of proteins has been the object of intense studies over the past decades, especially in the therapeutic field. -
Organocatalyzed Three-Component Ugi and Passerini Reactions of 4-Oxoazetidine-2
CORE Metadata, citation and similar papers at core.ac.uk Provided by Digital.CSIC Organocatalyzed Three-Component Ugi and Passerini Reactions of 4-Oxoazetidine-2- carbaldehydes and Azetidine-2,3-diones. Application to the Synthesis of -Lactams and -Lactones Benito Alcaide,*, † Pedro Almendros,‡ Cristina Aragoncillo,† Ricardo Callejo,† and M. Pilar Ruiz† †Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain, ‡Instituto de Química Orgánica General, IQOG, CSIC, Juan de la Cierva 3, 28006-Madrid, Spain, and [email protected] ABSTRACT X 2 1 H H 2 H H "ring-opening" R NHR R2 CHO "U-3CR" R NHR 3 "P-3CR" "cyclization" NHR 3 N O O N PhP(OH)2 (cat.) 1 X O R1 O R O 1 4 4 4 2 for: R NH2, X = NHR 6 X = NR 3 for: H2O, X = OH 7 X = O O O O O O H O HO H "P-3CR" 2 N PhP(OH) (cat.) R HN 1 2 N O R O R1 4 syn-5 Organocatalyzed U-3CR of 4-oxoazetidine-2-carbaldehydes has been studied. Besides, it the organocatalyzed P-3CR of 4-oxoazetidine-2-carbaldehydes and azetidine-2,3-diones has been described for the first time. U-3CR and P-3CR adducts have been obtained in good yields and reasonable diastereoselectivities. Phenyl phosphinic acid has been the catalyst of choice to study the scope of both organocatalyzed multicomponent reactions using a variety of -lactams, isocyanides and amines. -
An Exceptional Scientist and Human Being. in Memorial Ivar Ugi
HETEROCYCLES, Vol. 73, 2007 1 Ivar Ugi: An exceptional scientist and human being. In Memorial Ivar Ugi Ivar Ugi, a great scientist and exceptional human being recently left us. He died after a long and painful disease at the 27 September 2005. In memoriam Ivar Ugi this special issue of Heterocyles is edited with many contributions of his scientific friends and colleagues. He was born 1930 in Kuresare on the island Sareemma in Estonia. In 1941 the family Ugi left Estonia and moved to Dillingen an der Donau in Bavaria/Germany. There he went to high school. He studied mathematics and chemistry at the University of Tübingen. At the Ludwig Maximilian Universität in München he performed his PhD under the guidance of Prof. Rolf Huisgen. At the same university he performed his Habilitation “Isonitrile und Pentazole”. In 1962 he become married with his wife Helga and his son Ian was born. In the same year the family Ugi went to Leverkusen, where he joints the central research laboratory of the Bayer AG. Soon he became promoted to the “Research Director” and “Chairman of Bayer‘s Basic Research Committee”. During his time at Bayer Ivar Ugi and Otto Bayer became very good friends. However he realized that his managerial positions at Bayer mostly involved organisational work and prevented him from following his scientific ideas in the lab. Therefore, he was very lucky when he got a full chair for chemistry offered at the University of Southern California (USC) in the US. He stayed there form 1969 to 1971 and partially till 1973. -
Isocyanide-Based Multicomponent Reactions for the Synthesis of Heterocycles
Review Isocyanide-Based Multicomponent Reactions for the Synthesis of Heterocycles András Váradi, Travis C. Palmer, Rebecca Notis Dardashti and Susruta Majumdar * Received: 10 October 2015 ; Accepted: 17 December 2015 ; Published: 23 December 2015 Academic Editor: Romano V. A. Orru Department of Neurology, Memorial Sloan Kettering Cancer Center, New York, NY 10065, USA; [email protected] (A.V.); [email protected] (T.C.P.); [email protected] (R.N.D.) * Correspondence: [email protected]; Tel.: +1-646-888-3669 Abstract: Multicomponent reactions (MCRs) are extremely popular owing to their facile execution, high atom-efficiency and the high diversity of products. MCRs can be used to access various heterocycles and highly functionalized scaffolds, and thus have been invaluable tools in total synthesis, drug discovery and bioconjugation. Traditional isocyanide-based MCRs utilize an external nucleophile attacking the reactive nitrilium ion, the key intermediate formed in the reaction of the imine and the isocyanide. However, when reactants with multiple nucleophilic groups (bisfunctional reactants) are used in the MCR, the nitrilium intermediate can be trapped by an intramolecular nucleophilic attack to form various heterocycles. The implications of nitrilium trapping along with widely applied conventional isocyanide-based MCRs in drug design are discussed in this review. Keywords: Ugi reaction; heterocycles; nitrilium trapping 1. Introduction Multicomponent reactions are powerful tools for the rapid generation of molecular diversity and complexity. In a typical multicomponent process, more than two components are combined in a single reaction, thereby providing an operationally effective and highly modular approach towards the synthesis of structurally diverse molecular entities. Multicomponent reactions (MCRs) represent an excellent tool for the generation of libraries of small-molecule compounds and are indispensable for structure–activity relationship (SAR) studies. -
Multicomponent Reactions
Multicomponent reactions Edited by Thomas J. J. Müller Generated on 24 September 2021, 08:23 Imprint Beilstein Journal of Organic Chemistry www.bjoc.org ISSN 1860-5397 Email: [email protected] The Beilstein Journal of Organic Chemistry is published by the Beilstein-Institut zur Förderung der Chemischen Wissenschaften. This thematic issue, published in the Beilstein Beilstein-Institut zur Förderung der Journal of Organic Chemistry, is copyright the Chemischen Wissenschaften Beilstein-Institut zur Förderung der Chemischen Trakehner Straße 7–9 Wissenschaften. The copyright of the individual 60487 Frankfurt am Main articles in this document is the property of their Germany respective authors, subject to a Creative www.beilstein-institut.de Commons Attribution (CC-BY) license. Multicomponent reactions Thomas J. J. Müller Editorial Open Access Address: Beilstein J. Org. Chem. 2011, 7, 960–961. Heinrich-Heine-Universität Düsseldorf, Institut für Makromolekulare doi:10.3762/bjoc.7.107 Chemie und Organische Chemie, Lehrstuhl für Organische Chemie, Universitätsstr. 1, 40225 Düsseldorf, Germany Received: 11 July 2011 Accepted: 11 July 2011 Email: Published: 13 July 2011 Thomas J. J. Müller - [email protected] This article is part of the Thematic Series "Multicomponent reactions". Guest Editor: T. J. J. Müller © 2011 Müller; licensee Beilstein-Institut. License and terms: see end of document. Chemistry as a central science is facing a steadily increasing Now the major conceptual challenge comprises the engineering demand for new chemical entities (NCE). Innovative solutions, of novel types of MCR. Most advantageously and practically, in all kinds of disciplines that depend on chemistry, require new MCR can often be extended into combinatorial, solid phase or molecules with specific properties, and their societal conse- flow syntheses promising manifold opportunities for devel- quences are fundamental and pioneering. -
Recent Progress Concerning the N-Arylation of Indoles
molecules Review Review RecentRecent ProgressProgress Concerningconcerning the the NN-Arylation-Arylation of of Indoles Indoles Petr Oeser, Jakub Koudelka, Artem Petrenko and Tomáš Tobrman * Petr Oeser, Jakub Koudelka , Artem Petrenko and Tomáš Tobrman * Department of Organic Chemistry, University of Chemistry and Technology, 16628 Prague, Czech Republic; [email protected] of Organic (P.O.); Chemistry, [email protected] University of Chemistry (J.K.); [email protected] and Technology, 16628 (A.P.) Prague, Czech Republic; [email protected]* Correspondence: (P.O.); [email protected] [email protected] (J.K.); [email protected] (A.P.) * Correspondence: [email protected] Abstract: This review summarizes the current state-of-the-art procedures in terms of the prepara- Abstract:tion of N-arylindoles.This review summarizesAfter a short the intr currentoduction, state-of-the-art the transition-metal procedures-free in procedures terms of the available preparation for oftheN N-arylindoles.-arylation of After indoles a short are briefly introduction, discussed. the Th transition-metal-freeen, the nickel-catalyzed procedures and palladium-catalyzed available for the NN-arylation-arylation ofof indoles are brieflyboth discussed. discussed. In Then,the next the section, nickel-catalyzed copper-catalyzed and palladium-catalyzed procedures for the NN-arylation-arylation ofof indolesindoles areare bothdescribed. discussed. The final In the sectio nextn section,focuses copper-catalyzedon recent findings procedures in the field forof bio- the Nlogically-arylation active of indolesN-arylindoles. are described. The final section focuses on recent findings in the field of biologically active N-arylindoles. Keywords: N-arylation; indole; Buchwald–Hartwig amination; Ullmann condensation; Chan–Lam Keywords:coupling N-arylation; indole; Buchwald–Hartwig amination; Ullmann condensation; Chan– Lam coupling 1. -
The Biginelli and Related (Passerini and Ugi) Reactions
The Biginelli and Related (Passerini and Ugi) Reactions Mike DeMartino Group Meeting: August 27, 2003 Overview • How these reactions are related • The Biginelli Reaction – Mechanism – Modifications and chemical manipulation – Biology – Synthetic examples • The Passerini Reaction – Mechanism – Synthetic examples • The Ugi Reaction – Mechanism – Synthetic Reactions • Concluding Remarks Similarities • All are multicomponent Reactions (MCRs) • In MCRs, “three or more reactants come together in a single reaction vessel to form products that contain portions of all the components.” » Kappe, C. O. Acc. Chem. Res. 2000, 33, 879. • Has advantages over traditional linear syntheses. • Manifestations in a variety of chemical sects. The Biginelli Reaction The Biginelli Reaction • Synthesis of 3,4-dihydropyrimidin-2(1H)-ones was discovered in 1893 by Pietro Biginelli » Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360. EtO2C O + + O H2N NH2 O H + EtOH, H heat Ph => Biginelli-type EtO C 2 NH compounds Me N O H The Mechanism: a Century of Uncertainty • First proposal in 1933 » Folkers, K., Johnson, T.B. J. Am. Chem. Soc. 1933, 55, 3784. EtO C O 2 O O HN NH2 O 2 X + R H2N NH2 R H HN NH2 O O HO Me Ph CO Et HN N 2 EtO C 2 NH R H HN NH H O 2 2 Me N O H O The Mechanism: a Century of Uncertainty • Second proposal in 1973 » Sweet, F., Fissekis, J.D.. J. Am. Chem. Soc. 1973, 95, 8741. O EtO2C H + + H H O O O O HO O O OEt OEt OEt O H2N NH2 Ph CO Et HN 2 H O HN OEt O N Me O H H2O O NH2 The Mechanism: a Century of Uncertainty • Latest proposal in 1997 » Kappe, C.O. -
MCR XVII. Three Types of Mcrs and the Libraries – Their Chemistry of Natural Events and Preparative Chemistry
CROATICA CHEMICA ACTA CCACAA 71 (3) 527¿547 (1998) ISSN-0011-1643 CCA-2510 Conference Paper MCR XVII. Three Types of MCRs and the Libraries – Their Chemistry of Natural Events and Preparative Chemistry# Ivar Ugi,* Michael Almstetter, Holger Bock, Alexander Dömling, Birgit Ebert, Bernhard Gruber, Cordelia Hanusch-Kompa, Stefan Heck, Konstantina Kehagia-Drikos, Klaus Lorenz, Sofia Papathoma, Robert Raditschnig, Thomas Schmid, Birgit Werner, and Alexander von Zychlinski Technical University of Munich, Organic Chemistry I, Lichtenbergstr. 4, D-85747 Garching, Germany Received October 28, 1997; revised February 27, 1998; accepted April 10, 1998 The one-pot Multicomponent Reactions (MCRs)1 convert more than two different components into their products with at least two new chemical bonds, and the products contain all educts or at least some parts of them. Many chemical reactions have several, but not all, aspects of the MCRs. Three different basic types (I–III) and two subclasses (A and B) of MCRs can take place. Chemistry had started in the nature of our world roughly 4.6 billion years ago, in- cluding MCRs of the types I and II, forming libraries of many dif- ferent products. A little later, the living cells came into existence, and their biochemical MCRs of all three types started. In their various local parts their biochemical products are selectively formed by their enzyme-assisted procedures, but many of their MCRs belong to type III. The preparative chemistry of MCRs started in the middle of the last century, when the first equilibrating but isolateable 3CR prod- ucts of type IB were formed. The pre-final reactions of type I form compounds, which react further and form their final products irre- versibly by MCRs of type II. -
A Dissertation Entitled Applications of Ugi Four Component Cascade
A Dissertation entitled Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products by Amarendar Reddy Maddirala Submitted to the Graduate Faculty as partial fulfillment of the requirements for the Doctor of Philosophy Degree in Chemistry _________________________________________ Dr. Peter R. Andreana, Committee Chair _________________________________________ Dr. Joseph A. R. Schmidt, Committee Member _________________________________________ Dr. Jianglong Zhu, Committee Member _________________________________________ Dr. L. M. V. Tillekeratne, Committee Member _________________________________________ Dr. Patricia R. Komuniecki, Dean College of Graduate Studies The University of Toledo May, 2016 Copyright 2016, Amarendar Reddy Maddirala This document is copyrighted material. Under copyright law, no parts of this document may be reproduced without the expressed permission of the author. An Abstract of Applications of Ugi Four Component Cascade Coupling Reactions for the Synthesis of Bioactive Diverse Heterocyclic Molecules and Natural Products by Amarendar Reddy Maddirala Submitted to the Graduate Faculty as partial fulfillment of the requirements for the Doctor of Philosophy Degree in Chemistry The University of Toledo May, 2016 Isocyanide-based multicomponent reactions (IBMRs) have great advantages towards the assembly of complex molecules and are concise for the synthesis of higher ordered core structural motifs accomplished in a single synthetic