Advances in Organic Synthesis E-Book

• Herausgeber: Bentham Science Publishers
• Kategorie: Wissenschaft und neue Technologien
• Serie: Advances in Organic Synthesis
• Sprache: Englisch

Seitenzahl: 534

Veröffentlichungsjahr: 2022

Beschreibung

Advances in Organic Synthesis is a book series devoted to the latest advances in synthetic approaches towards challenging structures. The series presents comprehensive reviews written by eminent authorities on different synthetic approaches to selected target molecules and new methods developed to achieve specific synthetic transformations or optimal product yields. Advances in Organic Synthesis is essential for all organic chemists in academia and the industry who wish to keep abreast of rapid and important developments in the field.
Contents of this volume include these 7 reviews:
- Recent advances in copper-catalyzed heterocyclic syntheses
- Application of modern green chemistry methods in the synthesis of quinolines, quinazolines and quinazolinones
- Electroluminescence polymers-a review on synthesis by organic compounds
- Multicomponent approach for the synthesis of xanthenes
- From atoms to macromolecules: 100 years of polymer research
- An overview of oxidizing and reducing agents in total synthesis
- Amino acid-derived ionic liquids: novel biodegradable catalytic systems for green synthesis of heterocycles

Leseprobe

Table of Contents

BENTHAM SCIENCE PUBLISHERS LTD.

End User License Agreement (for non-institutional, personal use)

Usage Rules:

Disclaimer:

Limitation of Liability:

General:

PREFACE

List of Contributors

Recent Advances in Copper-catalyzed Heterocyclic Syntheses

Abstract

INTRODUCTION

CLASSIFICATION

Organic Compounds

Heterocyclic Compounds

GENERAL SYNTHESIS OF HETEROCYCLIC COMPOUNDS

CHEMISTRY & APPLICATIONS OF COPPER

RECENT TRENDS IN COPPER-CATALYZED HETEROCYCLIC SYNTHESES

Four Membered Heterocyclic Syntheses

Five-Membered Heterocyclic Syntheses

Six Membered and Higher Heterocyclic Synthesis

Condensed/Fused Heterocyclic Syntheses

CONCLUSION

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

Application of Modern Green Chemistry Methods in the Synthesis of Quinolines, Quinazolines and Quinazolinones

Abstract

INTRODUCTION

QUINOLINES

Microwave-assisted Synthesis

Ultrasound-assisted Synthesis

Mechanochemical and Solvent-free Synthesis

Synthesis in Deep Eutectic Solvents (DESs)

Synthesis in Ionic Liquids (ILs)

QUINAZOLINE

QUINAZOLINONE

Microwave-Assisted Synthesis

Ultrasound-assisted Synthesis

Mechanochemical and Solvent-free Synthesis

Synthesis in Ionic Liquids (ILs)

Synthesis in Deep Eutectic Solvents (DESs)

CONCLUSIONS AND PERSPECTIVES

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

Electroluminescence Polymers-a Review on Synthesis by Organic Compounds

Abstract

INTRODUCTION

Device Structure

The Physics Involving Oleds

Organic Semiconductors

SSH Model of an Electronic Structure

Mechanisms Used for Light Emission

Methods for Synthesising the Polymeric LEDs Using Organic Compounds

Thermo Conversion (Wessling–Zimmerman Route)

Chlorine Precursor Route (CPR)

Gilch Polycondensation

Non-ionic Route

Knoevenagel Polycondensation

Heck-Coupling Polymerisation

Wittig–Horner Condensation

Chemical Vapour Deposition (CVD)

Ring-Opening Metathesis Polymerisation (ROMP)

Miscellaneous

Conjugation Confinement

Conjugated-Non-Conjugated Block Copolymers (CNCP)s

Conjugated Polymers with Isolated Chromophores

Main Chain Polymers with a Defined Segmentation

Conjugated Main-chain Polymers with a Twisted Conformation

Conjugated Main Chain Polymers with the Non-conjugated Interruption

Soluble Conjugated Polymers Formed by Copolymerisation

Block and Graft Copolymers

Hyperbranched Conjugated Polymers

High-Efficiency Polymeric LEDs

Full-Colour and Colour Tuning PLED Displays

Degradation Phenomena in the PLEDs

Development of Polymeric Luminescent Materials

Polyfluorene-Based Luminescent Polymers

Polyfluorene Homopolymers

Polyfluorene Alternating Copolymers

Poly (p-phenylene Vinylene) and Derivatives

Poly (p-phenylene Vinylene) from Soluble Precursors

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

Multicomponent Approach for the Synthesis of Xanthenes

Abstract

INTRODUCTION

Synthesis of 1-Oxo-hexahydroxanthenes by Condensation of Cyclohexane-1,3-diones with Salicylaldehydes:

Synthesis of 13-Aryl-5H-dibenzo[b,i]xanthene-5,7,12,14(13H)-tetraones by Condensation of 2-Hydroxy-1,4-naphthoquinone and Aldehydes

Synthesis of 14H-Dibenzo[a,j]xanthenes by Condensation of 2-naphthol and Aldehydes

Synthesis of Spiro[dibenzo[b,i]xanthene-13,3′-indoline]-pentaones and spiro[dibenzo[b,i]xanthene-13,20-indene]-10,5,7,12,14-hexaones by Conden-sation of 2-Hydroxy-1,4-naphthoquinone and Isatin/Ninhydrin:

Synthesis of spiro[indoline-3,9’-xanthene]triones and Spiro[acenaph-thene-1, 9’-xanthene]-1’,2,8’(2’H,5’H)-triones by Condensation of 1,3-Cyclo- hexanediones and Isatin/Acenaphthene:

Synthesis of Tetrahydrobenzo[a]xanthene-11-ones by condensation of 2-Naphthol with Cyclohexane-1,3-dione derivatives and Aldehydes

Synthesis of Benzo[c]xanthenes By Condensation of 1-Naphthol, Aldehydes and Dimedone

Synthesis of 14-Aryl-14H-dibenzo[a,i]xanthene-8,13-diones by Conden-sation of 2-Hydroxy-1,4-naphthoquinone, Aldehydes and Substituted 2-naphthols

Synthesis 12-aryl-benzo[b]xanthene-1,6,11-triones by Condensation of 2-Hydroxy-1,4-naphthoquinone, Aldehydes and Cyclohexadione-1,3-diones:

Synthesis of [1, 3]Dioxolo[4,5-b]xanthenes by Condensation of Methylene-dioxyphenol and Aldehydes with 2-hydroxy-1,4-naphthoquinone and Dimedone

Synthesis of Spiro[dibenzo[a,i]-xanthene-14,30-indoline]-20,8,13-triones by Condensation of 2-Naphthol, Isatins and 2-hydroxy-1,4-naphthoquinone

Synthesis of (1H-Indol-3-yl)-Xanthen-4-(9H)-ones & 12-(Indol-3-yl) -12H-benzo[b]xanthene-6,11-diones by Coupling of 2-hydroxybenzaldehyde and indole with 5,5-dimethylcyclohexane-1,3-dione/2-hydroxy-1,4-naphtho quinone

Synthesis of Hexahydroxanthene-9-N-arylamines by Reaction of Cyclohexanone with Morpholine and Variously Substituted Salicylaldehyde Imines

Synthesis of Naphthoxanthenes by Condensation of 2-hydroxy-1,4-naphthoquinone and Salicylaldehyde with Thiophenols

Synthesis of Xanthene Derivatives by Condensation of o-trimethylsilyphenyl Triflate with Dimethylformamide and Dimedone

CONCLUSION

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

From Atoms to Macromolecules: 100 Years of Polymer Research

Abstract

INTRODUCTION

POLYMERS AND MACROMOLECULES: HISTORICAL BACKGROUND

STAUDINGER´S HYPOTESIS

The Best Way to Predict the Future is to Invent it

The Concept of Polymer

Polymers Have to be Macromolecules

CAROTHERS: POLYESTERS AND POLYCONDENSATION

WORLD WAR II: TEFLON, SYNTHETIC RUBBERS, AND THE SEARCHING OF POLYOLEFINS

ZIEGLER´S CATALYSTS AND NATTA´S TACTICITY OF POLYOLEFINS

SZWARC AND LIVING POLYMERS

PAUL FLORY: PRINCIPLES OF POLYMER SCIENCE

KAMINSKY AND METALLOCENES

THE SEARCHING OF “CONTROLLED” RADICAL POLYMERIZATIONS: NMP, ATRP, RAFT, AND MADIX

Nitroxide-Mediated Polymerization (NMP)

Atom Transfer Radical Polymerization (ATRP)

The Reversible Addition Fragmentation Transfer (RAFT) Mechanism

The RAFT Agent: Structure and Properties

GRUBB´S ACHIEVEMENTS: ROMP AND METHATHESIS POLYMERIZATION

CONDUCTING AND SEMICONDUCTING POLYMERS

A FEW WORDS ON THE SYNTHESIS OF BIOMACROMOLECULES

THE NEW ERA OF POLYMER SCIENCE

WHAT WILL LIFE BE LIKE FOR POLYMER RESEARCH SCIENTISTS AFTER THE COVID-19 PANDEMIC?

CONCLUDING REMARKS

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

An Overview of Oxidizing and Reducing Agents in Total Synthesis

Abstract

INTRODUCTION

Oxidation

Some of the Oxidizing Agents and their Applications

Tetrapropylammonium Perruthenate (TPAP)

TEMPO

Oxone

Sharpless Asymmetric Epoxidation and Dihydroxylation

Dess Martin Periodinane

Supported Gold/Silver Nanoparticles as Catalysts

Reduction

Some of the Reducing Agents and their Applications

DIBAL-H

Selectrides

Red Al/ Vitride

Crabtree’s Catalyst

Lithium Diisopropylamide (LDA)

Heterogeneous Silver (Ag) Nanoparticles as Catalysts

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

Amino Acid-derived Ionic Liquids: Novel Biodegradable Catalytic Systems for Green Synthesis of Heterocycles

Abstract

INTRODUCTION

AAILS AS CATALYSTS AND/OR SOLVENTS IN THE SYNTHESIS OF HETEROCYCLES

AAILs as Catalysts and/or Solvents in the Synthesis of Heterocycles in the Absence of other Solvents

AAILs as Catalysts in the Synthesis of Heterocycles in Aqueous Media

AAILs as Catalysts in the Synthesis of Heterocycles in Organic Solvents

BIONANOCOMPOSITES INCLUDED AAILS AS CATALYSTS IN THE SYNTHESIS OF HETEROCYCLES

CONCLUSION

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

Advances in Organic Synthesis

(Volume 16) 

Edited by

Atta-ur-Rahman, FRS

Kings College,

University of Cambridge,

Cambridge,

UK

BENTHAM SCIENCE PUBLISHERS LTD.

End User License Agreement (for non-institutional, personal use)

This is an agreement between you and Bentham Science Publishers Ltd. Please read this License Agreement carefully before using the ebook/echapter/ejournal (“Work”). Your use of the Work constitutes your agreement to the terms and conditions set forth in this License Agreement. If you do not agree to these terms and conditions then you should not use the Work.

Bentham Science Publishers agrees to grant you a non-exclusive, non-transferable limited license to use the Work subject to and in accordance with the following terms and conditions. This License Agreement is for non-library, personal use only. For a library / institutional / multi user license in respect of the Work, please contact: [email protected].

Usage Rules:

All rights reserved: The Work is the subject of copyright and Bentham Science Publishers either owns the Work (and the copyright in it) or is licensed to distribute the Work. You shall not copy, reproduce, modify, remove, delete, augment, add to, publish, transmit, sell, resell, create derivative works from, or in any way exploit the Work or make the Work available for others to do any of the same, in any form or by any means, in whole or in part, in each case without the prior written permission of Bentham Science Publishers, unless stated otherwise in this License Agreement.You may download a copy of the Work on one occasion to one personal computer (including tablet, laptop, desktop, or other such devices). You may make one back-up copy of the Work to avoid losing it.The unauthorised use or distribution of copyrighted or other proprietary content is illegal and could subject you to liability for substantial money damages. You will be liable for any damage resulting from your misuse of the Work or any violation of this License Agreement, including any infringement by you of copyrights or proprietary rights.

Disclaimer:

Bentham Science Publishers does not guarantee that the information in the Work is error-free, or warrant that it will meet your requirements or that access to the Work will be uninterrupted or error-free. The Work is provided "as is" without warranty of any kind, either express or implied or statutory, including, without limitation, implied warranties of merchantability and fitness for a particular purpose. The entire risk as to the results and performance of the Work is assumed by you. No responsibility is assumed by Bentham Science Publishers, its staff, editors and/or authors for any injury and/or damage to persons or property as a matter of products liability, negligence or otherwise, or from any use or operation of any methods, products instruction, advertisements or ideas contained in the Work.

Limitation of Liability:

In no event will Bentham Science Publishers, its staff, editors and/or authors, be liable for any damages, including, without limitation, special, incidental and/or consequential damages and/or damages for lost data and/or profits arising out of (whether directly or indirectly) the use or inability to use the Work. The entire liability of Bentham Science Publishers shall be limited to the amount actually paid by you for the Work.

General:

Any dispute or claim arising out of or in connection with this License Agreement or the Work (including non-contractual disputes or claims) will be governed by and construed in accordance with the laws of Singapore. Each party agrees that the courts of the state of Singapore shall have exclusive jurisdiction to settle any dispute or claim arising out of or in connection with this License Agreement or the Work (including non-contractual disputes or claims).Your rights under this License Agreement will automatically terminate without notice and without the need for a court order if at any point you breach any terms of this License Agreement. In no event will any delay or failure by Bentham Science Publishers in enforcing your compliance with this License Agreement constitute a waiver of any of its rights.You acknowledge that you have read this License Agreement, and agree to be bound by its terms and conditions. To the extent that any other terms and conditions presented on any website of Bentham Science Publishers conflict with, or are inconsistent with, the terms and conditions set out in this License Agreement, you acknowledge that the terms and conditions set out in this License Agreement shall prevail.

Bentham Science Publishers Pte. Ltd. 80 Robinson Road #02-00 Singapore 068898 Singapore Email: [email protected]

PREFACE

The 16th volume of Advances in Organic Synthesis presents recent exciting developments in synthetic organic chemistry. The chapters are written by eminent researchers in the field. The topics include advances in copper-catalyzed heterocyclic syntheses, modern green chemistry methods, review on electroluminescence polymers, synthesis of xanthene, evolution of polymer chemistry, and lastly, an overview on oxidizing and reducing agents in total synthesis.

This volume should prove to be a valuable resource for organic chemists, pharmaceutical scientists and postgraduate students seeking updated and critically important information on recent important developments in synthetic organic chemistry. I hope that the readers will find these reviews valuable and thought-provoking, and that they trigger further research in the quest for new developments in the field.

I am thankful to the efficient team of Bentham Science Publishers for the timely efforts, especially the editorial personnel Mr. Mahmood Alam (Editorial Director), Mr. Obaid Sadiq (Incharge eBooks Department), and Ms. Asma Ahmed (Manager Publications).

Prof. Atta-ur-Rahman, FRS Kings College University of Cambridge Cambridge UK

List of Contributors

E. Ciolino Andrés, Departamento de Ingeniería Química (DIQ)–Planta Piloto de Ingeniería Química (PLAPIQUI).Universidad Nacional del Sur – Consejo Nacional de Investigaciones Científicas y Técnicas de la República Argentina (UNS – CONICET)Bahía BlancaArgentinaJ. Satti Angel, Departamento de Química – Instituto de Química del Sur (INQUISUR)Universidad Nacional del Sur– Consejo Nacional de Investigaciones Científicas y Técnicas de la República Argentina (UNS – CONICET)Bahía BlancaArgentinaNallajarla Anil Kumar, Division of Chemistry, Department of Sciences and HumanitiesVignan’s Foundation for Science, Technology & Research (VFSTR) UniversityVadlamudi, Guntur522 213, Andhra PradeshIndiaChaudhary Ankita, Department of Chemistry, Maitreyi CollegeUniversity of Delhi, ChanakyapuriNew Delhi-110021Indiade Freitas Augusto G.O., Universidade Federal do Pampa – UNIPAMPAItaquiBrazilHaddad Batool Saleh, Department of Chemistry, College of ScienceUniversity of BasrahBasrahIraqSai Pavan Kumar Chebolu Naga Sesha, Division of Chemistry, Department of Sciences and HumanitiesVignan’s Foundation for Science, Technology & Research (VFSTR) UniversityVadlamudi, Guntur522 213, Andhra PradeshIndiaYielzoleh Fatemeh Molaei, Department of Chemistry, Faculty of Physics and ChemistryAlzahra UniversityP.O box 1993893973, Vanak, TehranIranBhalla Jitender, DAV CollegeSec. 10IndiaNikoofar Kobra, Department of Chemistry, Faculty of Physics and ChemistryAlzahra UniversityP.O box 1993893973, Vanak, TehranIranMolnar Maja, Josip Juraj Strossmayer University of OsijeFaculty of Food Technology OsijekFranje Kuhača 18, HR-31000 OsijekCroatiaD. Ninago Mario, Universidad Nacional de Cuyo (UNCuyo). Facultad de Ciencias Aplicadas a la Industria (FCAI).Consejo Nacional de Investigaciones Científicas y Técnicas de la República Argentina (CONICET).San RafaelArgentinaKomar Mario, Josip Juraj Strossmayer University of OsijeFaculty of Food Technology OsijekFranje Kuhača 18, HR-31000 OsijekCroatiaSadikha Shaik, Division of Chemistry, Department of Sciences and HumanitiesVignan’s Foundation for Science, Technology & Research (VFSTR) UniversityVadlamudi, Guntur522 213, Andhra PradeshIndiaHanoosh Widad Saleh, Department of Chemistry, College of ScienceUniversity of BasrahBasrahIraq

Recent Advances in Copper-catalyzed Heterocyclic Syntheses

Jitender Bhalla1,*

1 DAV College, Sec. 10, Chandigarh, India

Abstract

Heterocycles have gained significant attention from the research community due to their prevalence in numerous natural products and their applications as pharmaceuticals, agrochemicals, and new materials. The application of transition metal catalysts in the synthesis of heterocyclic compounds is an indispensable tool in the field of organic synthesis and has acquired notable recognition in scientific society all over the world. The popularity of copper-based catalysts is attributed to their cost-effectiveness, easy accessibility, and environmentally benign nature. In addition to this, the ability of copper catalysts to coordinate with heteroatoms and to activate unsaturated systems has resulted in the growing interest of synthetic and medicinal chemists in this field. Copper-based catalysts have shown their application in various cross-coupling reactions, C–H functionalization, radical alkylations, conjugate additions, and trifluoromethylation. Furthermore, they have also exhibited tremendous scope in heterocyclic syntheses, which include many important reactions, such as azide-alkyne click reaction (a type of 1,3-dipolar cycloaddition), nitrone-olefin cycloaddition (Kinugasa reaction), multi-component reactions, and other similar strategies which result in the construction of 4-8 membered heterocyclic adducts of biological and industrial relevance. The copper-catalyzed heterocyclic syntheses have many advantages, such as easily accessible substrates, good atom economy, high functional group tolerance, excellent yields, and remarkable selectivities. In addition to this, the targetted heterocycles exhibited diverse biological activities viz. antibacterial, antifungal, anticancer, antitubercular, anti-HIV, anti-inflammatory, analgesics, and antiviral activities. The main aim of this chapter is to summarize the advances made in copper-catalyzed synthesis of heterocyclic compounds in the last ten years.

Keywords: Asymmetric, Azide-alkyne cycloaddition, Click reaction, Copper-catalyzed, Cyclization, Cycloaddition, Diastereoselective, Enantioselective, Heterocycles, Heterocyclic syntheses, Kinugasa reaction, Multicomponent.

*Corresponding author Jitender Bhalla: DAV College, Sec. 10, Chandigarh, India; Tel: [phone]; E-mails: [email protected] and [email protected]