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    Dehydroacetic Acid and Its Derivatives: Useful Synthons in Organic Synthesis
    Dehydroacetic Acid and Its Derivatives: Useful Synthons in Organic Synthesis
    Dehydroacetic Acid and Its Derivatives: Useful Synthons in Organic Synthesis
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    Dehydroacetic Acid and Its Derivatives: Useful Synthons in Organic Synthesis

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    Dehydroacetic Acid and Its Derivatives: Useful Synthons in Organic Synthesis outlines the use of DHA and its derivatives for the synthesis of pharmacologically active heterocyclic compounds. Beginning with an introduction to the chemistry and reactivity of Dehydroacetic Acid, the book goes on to outline the key ring transformation reactions of DHA. The synthesis of various derivatives is then discussed, before a wide range of metal complexes of DHA are explored in detail. The book then concludes with a review of DHA’s biological importance and its impressive range of pharmacological activities, including anti-cancer, anti-bacterial, anti-fungal and analgesic properties.

    For those researching the synthesis of bioactive heterocyclic compounds, this book is a valuable guide on the fundamental knowledge needed to facilitate and enhance the successful synthesis of lead molecules.

    • Gives detailed information on the underlying chemistry of Dehydroacetic acid and its derivatives
    • Highlights different approaches for the synthesis of derivatives, including metal complexes
    • Explores the biological importance of Dehydroacetic Acid
    LanguageEnglish
    PublisherElsevier Science
    Release dateMar 31, 2017
    ISBN9780081019276
    Dehydroacetic Acid and Its Derivatives: Useful Synthons in Organic Synthesis

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      Dehydroacetic Acid and Its Derivatives - Santhosh Penta

      Dehydroacetic Acid and Its Derivatives

      Useful Synthons in Organic Synthesis

      Edited by

      Dr. Santhosh Penta, M.Sc., Ph.D

      Assistant Professor, Department of Chemistry, National Institute of Technology Raipur, Raipur, Chhattisgarh, India

      Table of Contents

      Cover image

      Title page

      Copyright

      List of Contributors

      Chapter 1. Introduction

      Abstract

      1.1 What Is Dehydroacetic Acid?

      1.2 Chemistry of Dehydroacetic Acid

      1.3 Reactivity

      1.4 Reactions at C3, C4, C5, and C6 Positions of DHA

      1.5 Other Reactions

      1.6 Applications

      Chapter 2. Ring Transformations in Dehydroacetic Acid

      Abstract

      2.1 Synthesis of Various Pyrazoles

      2.2 Synthesis of Bipyrazoles

      2.3 Isoxazoles, Pyrazolo-Pyrazoles, and Pyrazolones

      2.4 Synthesis of Pyrazolo-Oxazin-2-Thione Compounds

      2.5 Synthesis of Pyridones

      2.6 Synthesis of Pyrano Pyridineolates

      2.7 Synthesis of Pyridinol and Dimethyl Nicotinic Acid

      2.8 Synthesis of Various Pyrimidines

      2.9 Reactions That Modify the 2-Pyrone Skeleton

      2.10 Synthesis of Benzodiazepine, Benzodiazepinone, and Bezimidazoles

      Chapter 3. Synthesis of Different Heterocyclic Compounds by Using DHA

      Abstract

      3.1 Synthesis of Pyrazoles From Various Chalcones

      3.2 Synthesis of Substituted 2H-Pyran-2-Ones

      3.3 Synthesis of Various p-Tolylacryloyl Derivatives of DHA

      3.4 Classical Procedure for Synthesis of Phenylimino Derivatives of DHA

      3.5 Synthesis of DHA Substituted Thiazoles

      3.6 Synthesis of Diazepines

      3.7 Synthesis of Cinnamoyl Derivatives of DHA

      3.8 Synthesis of Various DHA Derivatives by Using the Multicomponent Approach

      Chapter 4. Dehydroacetic Acid–Metal Complexes

      Abstract

      4.1 Introduction and Importance of Fe Complexes

      4.2 Importance of Pt Complexes

      4.3 Importance of Cu Complexes

      4.4 Importance of Ru and Zn Complexes

      4.5 Pd (II) and Ni (II) Chelates of DHA

      4.6 Synthesis of Manganese Complexes From DHA

      4.7 Synthesis of Ruthenium (II) and Ruthenium (III) Complexes With DHA

      4.8 Synthesis of Cu (II), Co (II), Ni (II), and Cd (II) Complexes Using Sodium Salt of DHA

      4.9 Synthesis of Fe (III), Ni (II), Cu (II), Co (II), Mn (II), and Complexes by Using o-Phenylenediamine, DHA, and p-Chlorobenzaldehyde

      4.10 Synthesis of Fe (III), Co (II), Ni (II), Mn (II), and Cu (II) Complexes by Using DHA, 4-Methyl-o-Phenylene Diamine, and Salicylic Aldehyde

      4.11 Synthesis of Mn (II), Co (II), Ni (II), and Cu (II) Complexes From Phenyl Aniline–DHA Ligand

      4.12 Synthesis of Cr (III), Co (II), Oxo-Vanadium (IV), Mn (II), Fe (II), Cu (II), and Ni (II) Complexes From 1,2-Diaminoethane–DHA Ligand

      4.13 Synthesis of Ti (III), Cr (III), Fe (III), Mn (III), Zr (IV), VO (IV), and UO2 (VI) Complexes From DHA With 1,3-Diaminopropane

      4.14 Synthesis of Ni (II), Co (II) Complexes From Methanamine–DHA Ligand

      4.15 Synthesis of Mo (V) Complexes Using EHMPB and Tryptamine

      Chapter 5. Various Biological Activities of DHA Derivatives

      Abstract

      5.1 Introduction

      5.2 Anti-HIV Activity

      5.3 Anticancer Activity

      5.4 Antiliver Cancer Activity

      5.5 Antibacterial Activity

      5.6 Antifungal Activity

      5.7 Antiinflammatory Activity

      5.8 Phytotoxic Activity

      5.9 Analgesic Activity

      5.10 Photocleavage Activity

      References

      Index

      Copyright

      Elsevier

      Radarweg 29, PO Box 211, 1000 AE Amsterdam, Netherlands

      The Boulevard, Langford Lane, Kidlington, Oxford OX5 1GB, United Kingdom

      50 Hampshire Street, 5th Floor, Cambridge, MA 02139, United States

      Copyright © 2017 Elsevier Ltd. All rights reserved.

      No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording, or any information storage and retrieval system, without permission in writing from the publisher. Details on how to seek permission, further information about the Publisher’s permissions policies and our arrangements with organizations such as the Copyright Clearance Center and the Copyright Licensing Agency, can be found at our website: www.elsevier.com/permissions.

      This book and the individual contributions contained in it are protected under copyright by the Publisher (other than as may be noted herein).

      Notices

      Knowledge and best practice in this field are constantly changing. As new research and experience broaden our understanding, changes in research methods, professional practices, or medical treatment may become necessary.

      Practitioners and researchers must always rely on their own experience and knowledge in evaluating and using any information, methods, compounds, or experiments described herein. In using such information or methods they should be mindful of their own safety and the safety of others, including parties for whom they have a professional responsibility.

      To the fullest extent of the law, neither the Publisher nor the authors, contributors, or editors, assume any liability 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, instructions, or ideas contained in the material herein.

      British Library Cataloguing-in-Publication Data

      A catalogue record for this book is available from the British Library

      Library of Congress Cataloging-in-Publication Data

      A catalog record for this book is available from the Library of Congress

      ISBN: 978-0-08-101926-9

      For Information on all Elsevier publications visit our website at https://www.elsevier.com/books-and-journals

      Publisher: John Fedor

      Acquisition Editor: Anneka Hess

      Editorial Project Manager: Anneka Hess

      Production Project Manager: Paul Prasad Chandramohan

      Designer: Greg Harris

      Typeset by MPS Limited, Chennai, India

      List of Contributors

      Santhosh Penta,     National Institute of Technology Raipur, Raipur, Chhattisgarh, India

      Gudala Satish,     National Institute of Technology Raipur, Raipur, Chhattisgarh, India

      Archi Sharma,     National Institute of Technology Raipur, Raipur, Chhattisgarh, India

      Chapter 1

      Introduction

      Santhosh Penta,    National Institute of Technology Raipur, Raipur, Chhattisgarh, India

      Abstract

      3-Acetyl-4-hydroxy-6-methyl-2H-pyran, which is also known as dehydroaceticacid is a useful starting material for the synthesis of a wide variety of biologically active heterocyclic compounds. It was discovered by Geuther in 1866. It is a very popular compound in organic chemistry and exists in five tautomeric forms. In this chapter we will discuss about what is dehydroaceticacid…? constitution and structure, reactivity, biological importance and some important reactions from DHA.

      Keywords

      DHA; Reactivity; Constitution and structure; Phacidin; Podoblastin; Metal complexes; Cosmetic industry

      1.1 What Is Dehydroacetic Acid?

      Dehydroacetic acid (3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one) commercially abbreviated as DHA (1), is an important oxygen heterocyclic compound. It is well known for its various synthetic and physiological applications.

       Dehydroacetic acid is basically used as a bactericide and fungicide.

       It is utilized as a preserver to lessen pickle bloating for strawberries, squash, and different products.

       Sometimes, the salt form of dehydroacetic acid (known as sodium dehydroacetate) is used. This preservative shows excellent activity against fungi and has mild antibacterial properties.

      It has been reported that due to its excellent chelating capacity in modern coordination chemistry and also its reactions, DHA and its derivatives have a wide utility in the field of organic synthesis. DHA is used in the formulation of a wide variety of products including skin care products [1] (Fig. 1.1), suntan, sunscreen lotions, fragrance, bath products, shaving gels, hair and nail care products, as well as eye and facial makeup.

      Figure 1.1 Cosmetics. Ying G, Kurunthachalam K. A survey of phthalates and parabens in personal care products from the United States and its implications for human exposure. Environ Sci Technol 2013;47:14442−9.

      It is obtained from both natural [2–4] and synthetic sources and is mainly used to produce clopidol (2). It is a coccidiostatic agent (Fig. 1.2) and a food preservative [5].

      Figure 1.2 (A) Clopidol. (B) Coccidiosis in a goat ileum. Reza K, Saeid RN, Zeinab Y. J Parasit Dis, Indian Society for Parasitology. 2012. doi:10.1007/s12639-012-0186-0.

      Since the present investigation deals with the studies on the synthesis of some potential dehydroacetic acid derivatives, it would be more appropriate and necessary to present here a brief review on the chemistry of dehydroacetic acid.

      1.2 Chemistry of Dehydroacetic Acid

      1.2.1 Constitution and Structure

      DHA was discovered [6] in 1866 but ever since the discovery, the structure of DHA was a matter of great controversy. Two structures (1 and 3) were proposed by Fiest [7] and Collie [8].

      Its structure was resolved by Rassweiler and Adams [9] in 1924. They obtained the evidence to support Fiest’s structure and disprove the proposal given by Collie. DHA exists [10] as acetyl methyl pyrandione (4) in the solid state. It can exist in any of five tautomeric forms 4–8 [11] in the solution state which are represented below.

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