Multicomponent Reactions: Synthesis of Bioactive Heterocycles

409 Pages·2017·38.87 MB·English

by  K.L. Ameta Ph.D.

Multicomponent Reactions
Synthesis of Bioactive Heterocycles
http://taylorandfrancis.com
Multicomponent Reactions
Synthesis of Bioactive Heterocycles
Edited by
K. L. Ameta and Anshu Dandia
CRC Press
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Library of Congress Cataloging-in-Publication Data
Names: Ameta, K. L. | Dandia, Anshu.
Title: Multicomponent reactions : synthesis of bioactive heterocycles /
[edited by] K.L. Ameta and Anshu Dandia.
Description: Boca Raton : CRC Press, 2017. | Includes bibliographical
references and index.
Identifiers: LCCN 2016049529 | ISBN 9781498734127 (alk. paper)
Subjects: LCSH: Heterogeneous catalysis. | Heterocyclic compounds--Synthesis.
| Bioactive compounds. | Heterocyclic compounds.
Classification: LCC QD505 .M8475 2017 | DDC 547/.59--dc23
LC record available at https://lccn.loc.gov/2016049529
Visit the Taylor & Francis Web site at
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Contents
Preface......................................................................................................................vii
Editors .......................................................................................................................ix
Contributors ..............................................................................................................xi
Chapter 1 Synthesis of Pyridines by Multicomponent Reactions .........................1
Giammarco Tenti, M. Teresa Ramos, and J. Carlos Menéndez
Chapter 2 Isocyanide-Based Multicomponent Reactions Based
upon Intramolecular Nitrilium Trapping............................................33
Susruta Majumdar, András Váradi, and Travis C. Palmer
Chapter 3 The Role of Nanoporous Materials in Multicomponent
Synthesis/Modification of Heterocyclic Compounds .........................57
Esmail Doustkhah and Sadegh Rostamnia
Chapter 4 Multicomponent Reactions of Amino Acids and Their
Derivatives in Heterocycle Chemistry ...............................................83
Nahid S. Alavijeh, Somayeh Ahadi, and Saeed Balalaie
Chapter 5 Multicomponent Reactions for Generation of Molecular
Libraries in Anticancer Drug Discovery ..........................................117
Mohammad Saquib, Mohammad Faheem Khan,
Mohammad Imran Ansari, Irfan Khan,
Mohammad Kamil Hussain, and Jagdamba Singh
Chapter 6 Transition Metal Catalyzed Synthesis of Heterocycles
via Multicomponent Reactions .........................................................139
Satavisha Sarkar, Arghya Banerjee, and Bhisma K. Patel
Chapter 7 Synthesis of Fluorinated Heterocycles via Multicomponent
Reactions ...................................................................................183
Sandip S. Shinde, S. N. Thore, Rajendra P. Pawar, K. L. Ameta
and Sunil N. Patil
v
vi Contents
Chapter 8 One-Pot Total Synthesis of Bioactive Natural Products ..................201
Jiachen Xiang, Miao Wang, Yu Sun, and Anxin Wu
Chapter 9 Modern Synthesis of Bioactive Heterocycles via IMCR
Modification. .............................................................................229
Anshu Dandia, Shahnawaz Khan, Vijay Parewa, Amit Sharma,
and Begraj Kumawat
Chapter 10 Recent Progress on One-Pot, Multicomponent Reaction
for Pyridine Synthesis ......................................................................281
Vijaykumar Paike, Padmakar Suryavanshi, Sandeep More,
Sandeep B. Mane, Rajendra P. Pawar, and K. L. Ameta
Chapter 11 Synthesis of Functionalized Piperidine Derivatives Based
on Multicomponent Reaction ...........................................................299
Padmakar Suryavanshi, Vijaykumar Paike, Sandeep More,
Rajendra P. Pawar, Sandeep B. Mane, and K. L. Ameta
Chapter 12 Malononitrile: A Key Reagent for the Synthesis of Medicinally
Promising Fused and Spiro Pyridine Derivatives
in Multicomponent Reactions ..........................................................331
Ruby Singh and K. L. Ameta
Chapter 13 Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones/Thiones
and Polyhydroquinolines via Multicomponent Reactions ................369
Thomas J. Laughlin, Joshua S. Yoo, and Ram S. Mohan
Index ......................................................................................................................379
Preface
For many decades, biologically active heterocycles have been one of the main topics
of interest for medicinal chemists because they display a number of pharmacologi-
cal activities. Nitrogen, sulfur, and oxygen containing five- and six-membered het-
erocyclic compounds have been of enormous significance in the field of medicinal
chemistry. The majority of pharmaceuticals and biologically active agrochemicals
are heterocycles; countless additives and modifiers used in industrial applications,
such as cosmetics, reprography, information storage, and plastics, are heterocyclic
in nature.
A multicomponent reaction (MCR) is a process in which three or more easily
accessible components are combined in a single reaction vessel to produce a final
product. An MCR is a domino process, a sequence of elementary steps according
to a program in which subsequent transformations are determined by the function-
alities produced in the previous step. MCRs constitute an especially attractive syn-
thetic strategy since they provide easy and rapid access to large libraries of organic
compounds with diverse substitution patterns. As MCRs are one-pot reactions, they
are easier to carry out than multistep syntheses. In spite of the significant useful
attributes of MCRs for modern organic chemistry and their suitability for build-
ing up large compound libraries, these reactions were of limited interest in the past
50 years. However, in the last decade, with the introduction of high-throughput bio-
logical evaluation, the importance of MCRs for drug discovery has been recognized,
and considerable efforts from both academic and industrial researchers have been
focused especially on the design and development of multicomponent procedures for
the generation of various bioactive heterocycles. This growing interest is stimulated
by the significant therapeutic potential that is associated with many heterocycles.
Many of these techniques are reported in the reviews that you can read in the
chapters of this book. Thus, the purpose of the book is to provide a succinct sum-
mary of protocols for the synthesis of various differently sized bioactive heterocycles
using multicomponent reaction approaches.
We would like to thank all the authors who contributed so promptly to this book,
providing extraordinary reviews on the syntheses of different and highly valuable
bioactive heterocyclic compounds through the use of MCR. We trust that both under-
graduate and graduate students, as well as researchers and faculties, will find in these
pages an interesting guide and an updated state-of-the-art report on the enormous
versatility of MCR in the synthesis of bioactive heterocycles. We think that even an
expert in the research field will receive inspiration and motivation for future projects.
K. L. Ameta
Anshu Dandia
vii
http://taylorandfrancis.com
Editors
Dr. K. L. Ameta is an associate professor of chemistry at
the Department of Chemistry, College of Arts, Science and
Humanities, Mody University of Science and Technology,
Lakshmangarh, Rajasthan, India. He received his doctorate
degree in organic chemistry from M. L. Sukhadia University,
Udaipur, India, in 2002. He has published more than 50
research papers, 25 book chapters, and 6 edited books with
publishers of international repute. He has vast experience
in 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 interest in hetero-
geneous catalyzed organic synthesis and photocatalysis.
Dr. Anshu Dandia is a professor and head of the Department
of Chemistry, University of Rajasthan, Jaipur, India. She is
also the coordinator of the University Grants Commission–
Special Assistance Programme (UGC-SAP) at the University
of Rajasthan and vice president of the Indian Chemical Society,
Kolkata. Inducted as a fellow of the Royal Society of Chemistry
(FRSC), London, in 2012, Prof. Dandia has published over 170
research papers in the field of synthetic organic chemistry in
journals of international repute. Her fields of research interest are green and nanotech-
nology in organic synthesis; heterocyclic, medicinal chemistry; and organo-fluorine
chemistry. Her awards include the Science Legend Award from the World Science
Congress Association in 2015; the bronze medal awarded by the Chemical Research
Society of India, the Best Chemistry Teacher Award in India from Tata Chemicals
Ltd., Confederation of Indian Industries, and the Association of Chemistry Teachers,
all in 2012; International Distinguished Woman Scientist Award at the international
conference, “Chemistry for Mankind,” organized by the joint venture of American
Chemical Society (ACS), Royal Society of Chemistry (RSC), and Indian Society
of Chemists and Biologists (ISCB) at Nagpur in 2011; and the top researcher award
from the vice chancellor, University of Rajasthan, based on highest H-index in a sur-
vey done by DST New Delhi in 2009. Apart from this, she is a dedicated teacher and
strives to keep abreast of new developments in teaching methodologies.
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