Advances in Organic Synthesis: Volume 17 E-Book

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

Seitenzahl: 410

Veröffentlichungsjahr: 2002

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 6 reviews:
- Multicomponent synthesis of heterocycles by microwave irradiation
- Stereoselective procedures for the synthesis of olefines
- Advanced microwave assisted organic synthesis method in organic chemistry
- Five and six-membered n-heterocycle rings from diaminomaleonitrile
- Peptidomimetics: current and future perspectives on hiv protease inhibitors
- A review on synthesis, chemistry, and medicinal properties of benzothiazines and their related scaffolds

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

Multicomponent Synthesis of Heterocycles by Microwave Irradiation

Abstract

INTRODUCTION

Microwave Chemistry

Origin

Microwave Devices

Microwave Heating Mechanism

Dipolar Polarization Mechanism

Ionic Conduction Mechanism

Microwave Effects

Reaction-medium Effects

Specific Microwave Effects

Thermal Effects

Microwave Versus Classical Heating

Advantages and Disadvantages of the Microwave Heating

Microwave-Assisted Organic Synthesis

Multicomponent Reactions (MCRs)

Heterocyclic Compounds

Five – Membered Heterocycles

Five-Membered Heterocyclic Compounds with Single Heteroatoms

Five-Membered Heterocyclic Compounds with Two or More Heteroatoms

Six-membered Heterocycles

Six-membered Heterocyclic Compounds with Mono Heteroatom

Six-membered Heterocycles with Two Heteroatoms

Fused Heterocycles

CONCLUSION

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENT

List of Abbreviations

REFERENCES

Stereoselective Procedures for the Synthesis of Olefines

Abstract

INTRODUCTION

Isomerism in Alkenes

Cis v/s Trans Nomenclature

(E). ve (Z) Nomenclature

The Biological Significance of Alkenes

Synthesis of Alkenes and Stereoselectivity

The Elimination Reactions

The Reduction of Alkynes

The Julia Olefination

The Peterson Elimination

The Ramberg-Bäcklund Reaction

The Wittig Reaction

Olefin Metatez (Grubb’s Catalyst)

Metal Catalyzed Stereoselective Synthesis

CONCLUDING REMARKS

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENT

REFERENCES

Advanced Microwave Assisted Organic Synthesis Method in Organic Chemistry

Abstract

INTRODUCTION

MICROWAVE-ASSISTED ORGANIC SYNTHESIS IN AQUEOUS MEDIUM

Cross-Coupling Reaction

Suzuki-Miyaura Reaction

Sonogashira Reaction

Mizoroki – Heck Reaction

Preparation of Heterocyclic Compounds

Nitrogen-containing Heterocycles

Heterocycles Having Sulphur

Oxygen-containing Heterocyclic Compounds

Linkage of Carbon-Heteroatom

Preparation of Amides

Activation of C-H Group

Preparation of the Derivatives of Urea

7 Miscellaneous Reactions

OXIDATION

Oxidation of Alcohols

Microwave-Accelerated Oxidation of Cyclohexane

Microwave-accelerated Oxidation of 1- or 2-Phenylethanol

Microwave-Accelerated Oxidation of Hydroxymethyl Furfural to Added Value Compounds Over a Ruthenium-Based Catalyst

Microwave-Assisted Oxidation of Cyclohexane

REDUCTION

Reduction of Aldehydes and Ketones

Reduction of Nitroaromatic Compounds

Reduction of Nitro Compounds

Reduction of Ketones

Reduction of Organic Compounds

Reductive Amination

Cascade Reduction-Condensation Reactions

Reduction of Isatin

CONCLUSION

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

Acknowledgements

REFERENCES

Five and Six-membered N-heterocycle Rings from Diaminomaleonitrile

Abstract

INTRODUCTION

SYNTHESIS OF FIVE-MEMBERED RINGS

Synthesis of Imidazoles

Synthesis of 1,2,3-Triazoles

Synthesis of Telluradiazoles

SYNTHESIS OF SIX-MEMBERED RINGS

Synthesis of Pyrazines

Synthesis of Pyrimidines

CONCLUDING REMARKS

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

Peptidomimetics: Current and Future Perspectives on HIV Protease Inhibitors

Abstract

INTRODUCTION TO HIV GENOME

ANTIRETROVIRAL THERAPY AND SIGNIFICANCE OF PEPTIDOMIMETICS

SYNTHETIC APPROACHES TOWARDS SUBSTRATE-GUIDED HIV-1 PROTEASE INHIBITORS

Basis for the Substrate-Based Design of HIV Inhibitors

Synthetic Approaches to Peptidomimetics Against HIV-1 Protease

Synthetic Approaches Towards HIV-1 Protease Dimerization Inhibitors

SYNTHETIC APPROACHES TOWARDS HIV-1 TAT-TAR RNA INTERFACE INHIBITORS

SYNTHETIC APPROACHES TOWARDS HIV-1 CAPSID (CA) INHIBITORS

SYNTHETIC APPROACHES TOWARDS HIV-1 GLYCOPROTEIN GP120/GP41 INHIBITORS

SYNTHETIC APPROACHES TOWARDS OTHER HIV-1 INHIBITORS

CD4 Receptor Based Peptidomimetics

P6Gag Region-Tsg101 Serived Peptidomimetics

HIV-1 Coreceptor based Approaches for Peptidomimetics

Gelatinase-Based HIV Inhibitors

Prodrug Approaches for HIV-1 Protease Inhibitors

Miscellaneous HIV Inhibitors

THEORETICAL CALCULATIONS

STRATEGIES TO BE CONSIDERED IN DESIGN OF HIV-1/HIV-2 PROTEASE INHIBITORS

HIV-2 Protease and other Target-based Inhibitors

DISCUSSION

OPINIONS FROM OUR INTEREST

SUMMARY AND PERSPECTIVES

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

A Review on Synthesis, Chemistry, and Medicinal Properties of Benzothiazines and their Related Scaffolds

Abstract

INTRODUCTION

SYNTHESIS

1,2-Benzothiazine Derivatives

2,1-Benzothiazine Derivatives

1,3-Benzothiazine Derivatives

3,1-Benzothiazine Derivatives

1,4-Benzothiazine Derivatives

MEDICINAL PROPERTIES OF BENZOTHIAZINES

1,2-Benzothiazines

2,1-Benzothiazines

1,3-Benzothiazines

3,1-Benzothiazines

1,4-Benzothiazines

CONCLUSION

CONSENT FOR PUBLICATION

CONFLICT OF INTEREST

ACKNOWLEDGEMENTS

REFERENCES

Advances in Organic Synthesis

(Volume 17)

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 book/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 17th 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 multicomponent synthesis of heterocycles by microwave irradiation, stereoselective procedures for the synthesis of olefins, advanced microwave-assisted organic synthetic method in organic chemistry, synthesis of five and six-membered N-heterocycle rings from diaminomaleonitrile, current and future perspectives of peptidomimetics on HIV protease inhibitors, and methods to synthesize benzothiazines and their derivatives.

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 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

Abdulrahman S. AlharbiDepartment of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, KSA Department of Pharmaceutical Chemistry, Faculty of Pharmacy, King Abdulaziz University, Jeddah, KSAAbeer N. Al-RomaizanDepartment of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, KSAAlice Rinky RobertDepartment of Chemistry, GITAM Institute of Sciences, GITAM (deemed to be University), Visakhapatnam, Andhra Pradesh, IndiaAmal Al-AzmiChemistry Department, Kuwait University, P. O. Box 5969, Safat-13060, KuwaitAnamika SrivastavaDepartment of Chemistry, Banasthali Vidyapith, Banasthali-304022 (Rajasthan), IndiaAnjali BangerDepartment of Chemistry, Banasthali Vidyapith, Banasthali-304022 (Rajasthan), IndiaGanja HimavathiSchool of Chemistry & Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills, Durban 4000, South AfricaHaydar GöksuKaynasli Vocational College, Düzce University, Düzce, TurkeyJaya DwivediDepartment of Chemistry, Banasthali Vidyapith, Banasthali-304022 (Rajasthan), IndiaKiranmai NayaniDepartment of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, IndiaMaddila SureshDepartment of Chemistry, GITAM Institute of Sciences, GITAM (deemed to be University), Visakhapatnam, Andhra Pradesh, India School of Chemistry & Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills, Durban 4000, South AfricaManish SrivastavaDepartment of Chemistry, Banasthali Vidyapith, Banasthali-304022 (Rajasthan), IndiaPrathama S MainkarDepartment of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, IndiaRavina YadavAmity School of Applied Sciences, Amity University Haryana, Gurugram-122413 (Haryana), IndiaReda M. Abdel-RahmanDepartment of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, KSAVarun RawatSchool of Chemistry, Tel Aviv University, Tel Aviv-6997801, Israel

Multicomponent Synthesis of Heterocycles by Microwave Irradiation

Alice Rinky Robert1,Ganja Himavathi2,Maddila Suresh1,2,*

1 Department of Chemistry, GITAM Institute of Sciences, GITAM (deemed to be University), Visakhapatnam, Andhra Pradesh, India

2 School of Chemistry & Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills, Durban 4000, South Africa

Abstract

The multicomponent reactions (MCRs) are vital for producing structurally varied molecular objects. Multicomponent reactions (MCRs) contain three or more synthetic stages and are carried out without isolation of any intermediate, thus requiring mild reaction conditions. They are eco-friendly and cost-effective, have a short reaction time, produce higher yields, and require raw materials. The use of microwave irradiation in green organic synthesis sustains some of the aims of “green and sustainable chemistry.” It offers several benefits over the conventional approach in reducing time, reaction rates, selectivity, product yields, etc. Consequently, the preparation of various heterocycles using a one-pot multicomponent method combined with the application of microwave irradiation is one of the best areas amongst synthetic chemistry. The present study illustrates an overview of recent progress on microwave-irradiated, one-pot multicomponent synthesis of heterocycles.

Keywords: Benzoxazoles, Conventional Heating, Furans, Fused Heterocycles, Green Chemistry, Heating Mechanism, Heterocyclic Compounds, Imidazoles, Multicomponent Synthesis, Microwave Effects, Microwave Irradiation, One-pot Reaction, Pyrans, Pyridines, Pyrimidines, Pyrroles, Reaction selectivity, Spiro-heterocycles, Thiazoles, Triazoles.

*Corresponding author Suresh Maddila: School of Chemistry and Physics, University of KwaZulu-Natal, Westville Campus, Chiltern Hills, Durban-4000, South Africa; E-mail: [email protected]