Green Chemistry: Synthesis of Bioactive Heterocycles

K. L. Ameta • Anshu DandiaEditors

Green Chemistry: Synthesis of Bioactive Heterocycles

1 3

ISBN 978-81-322-1849-4 ISBN 978-81-322-1850-0 (eBook)DOI 10.1007/978-81-322-1850-0Springer New Delhi Heidelberg New York Dordrecht London

Library of Congress Control Number: 2014939029

© Springer India 2014This work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed. Exempted from this legal reservation are brief excerpts in connection with reviews or scholarly analysis or material supplied specifically for the purpose of being entered and executed on a computer system, for exclusive use by the purchaser of the work. Du-plication of this publication or parts thereof is permitted only under the provisions of the Copyright Law of the Publisher’s location, in its current version, and permission for use must always be obtained from Springer. Permissions for use may be obtained through RightsLink at the Copyright Clearance Center. Violations are liable to prosecution under the respective Copyright Law.The use of general descriptive names, registered names, trademarks, service marks, etc. in this publica-tion does not imply, even in the absence of a specific statement, that such names are exempt from the relevant protective laws and regulations and therefore free for general use.While the advice and information in this book are believed to be true and accurate at the date of publica-tion, neither the authors nor the editors nor the publisher can accept any legal responsibility for any errors or omissions that may be made. The publisher makes no warranty, express or implied, with respect to the material contained herein.

Printed on acid-free paper

Springer is part of Springer Science+Business Media (www.springer.com)

EditorsK. L. AmetaChemistryMITS UniversityLakshmangarhRajasthanIndia

Anshu DandiaChemistryUniversity of RajasthanJaipurRajasthanIndia

v

Preface

Since many decades, research on bioactive heterocycles is one of the main topics of interest for the medicinal chemists because of a number of pharmacological activi-ties of this class of compounds. Nitrogen, sulphur and oxygen containing five- and six-membered heterocyclic compounds, but even smaller or larger cyclic structures, have occupied enormous significance in the field of medicinal chemistry. The ma-jority of pharmaceuticals and biologically active agrochemicals are heterocycles while countless additives and modifiers used in industrial applications ranging from cosmetics, reprography, information storage and plastics are heterocyclic in nature. One striking structural feature inherent to heterocycles, which continues to be exploited to great advantage by the drug industry, lies in their ability to manifest substituent’s around a core scaffold in defined three-dimensional representations. For more than a century, heterocycles have constituted one of the largest areas of research in organic chemistry.

In the recent years a renewed sensitivity to the environmental problems con-nected with the organic syntheses was the driving force that moves the chemists to introduce novel techniques and particularly eco-friendly procedures. Atom-econ-omy and minimization of side products formation, solvent less conditions, use of unconventional techniques to run reactions (microwave, ultrasound, ball-milling, ionic liquids, etc) were introduced and play a relevant role in today chemistry labs and will be probably more intensively and massively used in the synthetic labs in the next future.

Green chemistry uses highly efficient and environmental benign synthetic proce-dures to synthesize various bioactive heterocyclic frameworks which are the useful synthons for the synthesis of medicines, plastics, petrochemicals, agrochemicals, cosmetics and many more. Green chemistry has been defined as a set of principles that reduces or eliminates the use or generation of hazardous substances throughout the entire life of chemical materials [1, 2]. Green chemistry offers enhanced chemi-cal process economics concomitant with a reduced environmental burden. Green sustainable chemistry (GSC) is defined as the chemistry and chemical technology for eco-friendly products and processes.

Thus, the purpose behind writing this book is to provide a succinct summary of various green chemistry approaches for the synthesis and biological activities of different bioactive heterocycles.

vi Preface

[1] Anastas PT, Warner JC (1998) Green chemistry, theory and practice. Oxford University Press, New York

[2] Clark JH (1999) Forum. Green Chem 1(1):G1–G2

K. L. Ameta Anshu Dandia

AQ1

vii

Contents

1 Synthesis of Heterocycles Through Multicomponent Reactions in Water ................................................................................... 1Pethaiah Gunasekaran, J. Carlos Menéndez and Subbu Perumal

2 Sustainable Approaches Towards the Synthesis of Quinoxalines ........ 37Pradeep S. Jadhavar, Dinesh Kumar, Priyank Purohit, Bhavin V. Pipaliya, Asim Kumar, Srikant Bhagat and Asit K. Chakraborti

3 Eco-Friendly Synthesis of Bioactive Heterocycles ................................ 69Ali Gharib

4 Ammonium- and Phosphonium-Based Ionic Liquid: Green and Reusable Catalysts ............................................................................ 105Swapanil R. Sarda, Sunil K. Wasmatkar, Wamanrao N. Jadhav, Satish A. Dake, Anjan R. Sawale, Niteshkumar S. kaminwar, Suresh U. Shisodia and Rajendra P. Pawar

5 An Approach Towards Green Switch Through Nanocatalysis for the Synthesis of Biodynamic Heterocycles ....................................... 129Anshu Dandia, Vijay Parewa and Amit Sharma

6 Microwave-Induced Synthesis of Various Quinoline Derivatives: Green Methodologies in Organic Synthesis ..................... 163N. C. Desai and Amit M. Dodiya

7 Imidazolium Ionic Liquids: An Environment-Friendly Medium for Various Applications ........................................................... 201Satish A. Dake, Swapanil R. Sarda, Rajendra P. Marathe, Rajesh B. Nawale, Uday A. Deokate, Somshekhar S. Khadabadi and Rajendra P. Pawar

viii Contents

8 Water: A Benign Solvent for the Synthesis of Various Organic Moieties ...................................................................................... 231Chetna Ameta and K. L. Ameta

9 Synthesis and Synthetic Applications of Biologically Interesting Rhodanine and Rhodanine-Based Scaffolds ...................... 253Sadegh Rostamnia and Esmail Doustkhah

10 Molecular Iodine: Mild, Green, and Nontoxic Lewis Acid Catalyst for the Synthesis of Heterocyclic Compounds ........................ 277Anshu Dandia, Shyam L. Gupta and Shuchi Maheshwari

11 Microwave Radiations: A Tool for the Synthesis of Heterocycles in an Ecofriendly Manner ................................................. 329Shipra Bhardwaj and K. L. Ameta

12 Green Chemistry Approach Using Heterogeneous Catalysts in the Heterocyclic Synthesis ................................................................... 367Sudesh Kumar, Prachi Rathi, K. L. Ameta and Dharma Kishore

13 Synthesis and Biological Evaluation of Some Quinazoline Heterocyclic Derivatives .......................................................................... 393R. R. Dangi, N. S. Chundawat and K. L. Ameta

ix

Chetna Ameta Department of Chemistry, University College of Science, MLS University, Udaipur, Rajasthan, India

K. L. Ameta Department of Chemistry, FASC, Mody University of Science and Technology, Lakshmangarh, Rajasthan, India

Srikant Bhagat Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali, Punjab, India

Shipra Bhardwaj Government P. G. College, Kota, Rajasthan, India

Asit K. Chakraborti Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali, Punjab, India

N. S. Chundawat Department of Chemistry, FASC, Mody University of Science and Technology, Lakshmangarh, Rajasthan, India

Satish A. Dake Department of Chemistry, Deogiri College, Aurangabad, Maharashtra, India

Anshu Dandia Centre of Advanced Studies, Department of Chemistry, University of Rajasthan, Jaipur, India

Centre of Advanced Studies, Department of Chemistry, University of Rajasthan, Jaipur, Rajasthan, India

R. R. Dangi Department of Chemistry, FASC, Mody University of Science and Technology, Lakshmangarh, Rajasthan, India

Uday A. Deokate Government College of Pharmacy, Aurangabad, Maharashtra, India

N. C. Desai Department of Chemistry, UGC NON-SAP & DST-FIST Sponsored Department, Mahatma Gandhi Campus, Maharaja Krishnakumarsinhji Bhavnagar University, Bhavnagar, Gujarat, India

Amit M. Dodiya Department of Chemistry, UGC NON-SAP & DST-FIST Sponsored Department, Mahatma Gandhi Campus, Maharaja Krishnakumarsinhji Bhavnagar University, Bhavnagar, Gujarat, India

Contributors

x Contributors

Esmail Doustkhah Organic and Nano Group (ONG), Department of Chemistry, University of Maragheh, Maragheh, Iran

Ali Gharib Department of Organic Chemistry, Agricultural Research and Service Center and Department of Chemistry, Islamic Azad University, Mashhad, Iran

Pethaiah Gunasekaran Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, India

Shyam L. Gupta Centre of Advanced Studies, Department of Chemistry, University of Rajasthan, Jaipur, Rajasthan, India

Wamanrao N. Jadhav Department of Chemistry, Dnyanopasak College, Parbhani, Maharashtra, India

Pradeep S. Jadhavar Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali, Punjab, India

Niteshkumar S. Kaminwar Department of Chemistry, Deogiri College, Aurangabad, Maharashtra, India

Somshekhar S. Khadabadi Government College of Pharmacy, Aurangabad, Maharashtra, India

Dharma Kishore Department of Chemistry, Banasthali University, Banasthali, Rajasthan, India

Asim Kumar Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali, Punjab, India

Dinesh Kumar Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali, Punjab, India

Sudesh Kumar Department of Chemistry, Banasthali University, Banasthali, Rajasthan, India

Shuchi Maheshwari Centre of Advanced Studies, Department of Chemistry, University of Rajasthan, Jaipur, Rajasthan, India

Rajendra P. Marathe Government College of Pharmacy, Aurangabad, Maharashtra, India

J. Carlos Menéndez Facultad de Farmacia, Departamento de Química Orgánica y Farmacéutica, Universidad Complutense, Madrid, Spain

Rajesh B. Nawale Government College of Pharmacy, Aurangabad, Maharashtra, India

Vijay Parewa Centre of Advanced Studies, Department of Chemistry, University of Rajasthan, Jaipur, India

Rajendra P. Pawar Department of Chemistry, Deogiri College, Aurangabad, Maharashtra, India

Government College of Pharmacy, Aurangabad, Maharashtra, India

xiContributors

Subbu Perumal Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, India

Bhavin V. Pipaliya Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali, Punjab, India

Priyank Purohit Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Mohali, Punjab, India

Prachi Rathi Department of Chemistry, Banasthali University, Banasthali, Rajasthan, India

Sadegh Rostamnia Organic and Nano Group (ONG), Department of Chemistry, University of Maragheh, Maragheh, Iran

Swapanil R. Sarda Department of Chemistry, J. E. S. College, Jalna, Maharashtra, India

Anjan S. Sawale Department of Chemistry, Deogiri College, Aurangabad, Maharashtra, India

Amit Sharma Centre of Advanced Studies, Department of Chemistry, University of Rajasthan, Jaipur, India

Suresh U. Shisodia Department of Chemistry, Deogiri College, Aurangabad, Maharashtra, India

Sunil K. Wasmatkar Department of Chemistry, Dnyanopasak College, Parbhani, Maharashtra, India

xiii

About the Editors

Dr. (Mrs.) Anshu Dandia is working as Professor at Department of Chemistry, University of Rajasthan, Jai-pur. Also, she is Coordinator, UGC-SAP Programme and Director, P. G. School of Physical Sciences and Affairs, Vigyan Bhawan, University of Rajasthan, Jaipur. Prof. Dandia has published over 160 research papers in the field of synthetic organic chemistry in the journals of interna-tional repute. Her fields of research interest are green and nanotechnology in organic synthesis, heterocyclic and medicinal chemistry and organo-fluorine chemistry. Moreover, she is honored as “Fellow of Royal Society

of Chemistry (FRSC)”, London in 2012; “Bronze medal” awarded by Chemical Research Society of India in 2012; “International Distinguished Women Scien-tist Award” in the international conference on “Chemistry for Mankind” organized by the joint venture of ACS, RSC and ISCB at Nagpur in 2011; “Top Researcher” award by the Vice Chancellor, University of Rajasthan based on highest H-index in the survey done by DST New Delhi in 2009. Apart from this, she is a dedicated teacher and strives to be abreast of new developments in teaching methodologies and she has received “Best Chemistry Teacher Award” in India by Tata Chemicals Ltd., Confederation of Indian Industries and the Association of Chemistry Teachers in Nov, 2012.

Dr. K. L. Ameta received his doctorate degree in Organic Chemistry from M. L. Sukhadia University, Udaipur, India in the year 2002. Presently, he is working as Assis-tant Professor of Chemistry, Faculty of Arts, Science and Commerce, Mody Institute of Technology and Science (Deemed University) Lakshmangarh, Rajasthan, India. He has vast experience of teaching both graduate and postgraduate level students. His research area involves synthesis, characterization and biological evaluation of different sized bioactive heterocyclic systems. In addition

to this, he has keen interests in heterogeneous catalyzed organic synthesis and pho-tocatalysis. He has published a number of research articles in various journals of national and international repute.