Nanocatalysis: Synthesis of Bioactive Heterocycles

269 Pages·2022·32.765 MB·English

by  Keshav Lalit Ameta, Ravi Kant

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Nanocatalysis
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Nanocatalysis
Synthesis of Bioactive Heterocycles
Edited by Keshav Lalit Ameta and Ravi Kant
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First edition published 2022
by CRC Press
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© 2022 selection and editorial matter, Keshav Lalit Ameta and Ravi Kant; individual chapters, the contributors
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ISBN: 9780367693541 (hbk)
ISBN: 9780367693558 (pbk)
ISBN: 9781003141488 (ebk)
DOI: 10.1201/ 9781003141488
Typeset in Times
by Newgen Publishing UK
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Contents
List of Figures ..................................................................................................................................vii
List of Tables .....................................................................................................................................ix
Preface ...............................................................................................................................................xi
Contributors ....................................................................................................................................xiii
About the Editors .............................................................................................................................xv
Chapter 1 Nanocatalysed Synthesis of Lactams ...........................................................................1
R. Chandran and A. Sharma
Chapter 2 Recent Advances in Nanocatalyzed Synthesis of Seven- Member
N- Heterocyclic Compounds with Special Reference to Azepines,
Benzoazepines, Benzodiazepines, and Their Derivatives: A Brief Review ...............25
R. M. Borade, S. B. Kale, S. U. Tekale, C. S. Patil, S. B. Ubale,
Keshav Lalit Ameta, and R. P. Pawar
Chapter 3 An Overview of the Synthesis of Pyrroline, Indolizine, and Quinolizinium
Derivatives Using Different Nanocatalysts ................................................................53
R. N. Shelke, A. B. Kanagare, S. U. Deshmukh, S. R. Bembalkar,
D. N. Pansare, Keshav Lalit Ameta, and R. P. Pawar
Chapter 4 Nanocatalyzed Synthesis of Bioactive Pyrrole, Indole, Furan, and Benzofuran
Derived Heterocycles .................................................................................................75
S. U. Deshmukh, Ajit K. Dhas, Vidya D. Dofe, Satish A. Dake,
Jaiprakash N. Sangshetti, Keshav Lalit Ameta, and R. P. Pawar
Chapter 5 Cheaper Transition Metals- Based Nanocatalyzed Organic Transformations and
Synthesis of Bioactive Heterocycles: Strategic Approaches and Sustainable
Applications ...............................................................................................................95
Ravi K. Yadav, Vedant V. Deshmukh, Tushar M. Boralkar, Mukesh Jain,
and Sandeep Chaudhary
Chapter 6 Nanocatalysis: An Efficient Tool for the Synthesis of Triazines and Tetrazines ......127
A. B. Kanagare, D. N. Pansare, Ajit K. Dhas, Rajita D. Ingle,
R. N. Shelke, Keshav Lalit Ameta, and R. P. Pawar
Chapter 7 Synthesis of Quinolines, Isoquinolines, and Quinolones Using Various
Nanocatalysts............................................................................................................147
Chetna Ameta, Yogeshwari Vyas, Purnima Chaubisa, Dharmendra,
and Keshav Lalit Ameta
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vi Contents
Chapter 8 Recent Advances in Nanocatalyzed Synthesis of Triazoles and Tetrazoles
and Their Biological Studies ....................................................................................177
Popat M. Jadhav, A. B. Kanagare, Anand B. Dhirbassi, Atam B. Tekale,
R. M. Borade, S. U. Tekale, Keshav Lalit Ameta, and R. P. Pawar
Chapter 9 Nanocatalysed Synthesis and Biological Significance of Imidazoles,
Hydantoins, Oxazoles, and Thiazoles ......................................................................201
Surbhi Dhadda, Nidhi Jangir, Shikha Agarwal, Arvnabh Mishra,
and Dinesh Kumar Jangid
Chapter 10 Nanocatalysed Synthesis of Pyrazoles, Indazoles, and Pyrazolines ........................219
Divyani Gandhi, Ayushi Sethiya, Nusrat Sahiba, Dinesh Kumar Jangid,
and Shikha Agarwal
Index ..............................................................................................................................................245
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Figures
Figure 1.1 Class of lactams ...........................................................................................................2
Figure 1.2 Biologically active lactam containing drugs................................................................3
Figure 1.3 Application of Cu- based nano particles ......................................................................8
Figure 1.4 Substrate scope ............................................................................................................9
Figure 1.5 Plausible mechanism .................................................................................................10
Figure 1.6 Plausible mechanism of reaction ...............................................................................13
Figure 1.7 Plausible mechanism of reaction ...............................................................................15
Figure 1.8 Plausible mechanism of reaction ...............................................................................17
Figure 1.9 Plausible mechanism of reaction ...............................................................................18
Figure 2.1 Bioactive azepine derivatives .....................................................................................26
Figure 2.2 Alkaloids containing bioactive benzapine derivatives ...............................................27
Figure 2.3 Bioactive benzazepine derivatives .............................................................................27
Figure 2.4 Some of the BZD- based drugs available in the market .............................................29
Figure 2.5 Proposed reaction pathway for the synthesis of 1,5- benzodiazepin- 2- ones
by CuI NPs ................................................................................................................31
Figure 2.6 Structural framework of catalyst MIL/ K- SOH .........................................................35
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Figure 2.7 Structure of K 22 .......................................................................................................42
Figure 3.1 Structural isomers of the pyrrolines...........................................................................54
Figure 3.2 Selected examples of biologically active 1- pyrrolines ..............................................54
Figure 3.3 Indolizine derivative ..................................................................................................60
Figure 3.4 Pyrido- fused- indolizine derivative.............................................................................60
Figure 3.5 Indolizine- esters ........................................................................................................61
Figure 3.6 Indolizine derivatives .................................................................................................61
Figure 3.7 Indolizine derivatives .................................................................................................62
Figure 3.8 Indolizine derivatives .................................................................................................63
Figure 3.9 Structures of indolizines derivatives ..........................................................................64
Figure 4.1 Some bioactive pyrrole systems ................................................................................76
Figure 4.2 Pyrrole that contains active drugs ..............................................................................77
Figure 5.1 Mechanistic pathway for the reversible ADH of 2- methyl- 1,2,3,4-
tetrahydroquinoline ....................................................................................................98
Figure 8.1 Structures biologically active compounds containing triazoles and
tetrazoles ..................................................................................................................180
Figure 9.1 N, S and O containing heterocycles and their biological significance ....................202
Figure 9.2 The structure of imidazole (a) and benzimidazole (b) .............................................203
Figure 9.3 Resonance hybrid of (a) imidazole and (b) benzimidazole .....................................203
Figure 9.4 Some biologically active imidazole and benzimidazole derivatives .......................206
Figure 9.5 The structure of hydantoin .......................................................................................206
Figure 9.6 Some biologically active hydantoin derivatives ......................................................209
Figure 9.7 Structure of (a) oxazole and (b) benzoxazole ..........................................................210
Figure 9.8 Resonance hybrid of (a) oxazole and (b) benzoxazole ............................................210
Figure 9.9 Structure of bioactive benzoxazoles ........................................................................212
Figure 9.10 Structure of (a) thiazole and (b) benzothiazole .......................................................212
Figure 9.11 Resonance hybrid of (a) thiazole and (b) benzothiazole .........................................212
Figure 9.12 Structure of bioactive thiazoles and benzothiazoles ................................................215
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viii Figures
Figure 10.1 Marketed drugs containing pyrazole heterocycles as the core structural unit .........220
Figure 10.2 Tautomeric forms of indazoles ................................................................................221
Figure 10.3 Approved drugs with an indazole core and pharmaceutical properties ...................222
Figure 10.4 Types of pyrazoline..................................................................................................222
Figure 10.5 Some pharmacologically active drug molecules containing a
pyrazoline nucleus ...................................................................................................223
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Tables
Table 1.1 Supported gold catalyst and its application in functional group
conversion ......................................................................................................................4
Table 2.1 Various benzazepine derivatives (5) synthesized in acidic solution of
HO using KF/ CP nanocomposite ..............................................................................28
2 2
Table 7.1 Yield corresponding to various combinations ............................................................149
Table 7.2 Various acid and aminoaryl ketones used to produce quinolones ..............................150
Table 7.3 Effect of various 2- nitobenzaldehyde on yield of product .........................................153
Table 7.4 Synthesis of derivatives of quinoline that used FeO@SiO/ isoniazid/ Cu(II) via
3 4 2
Friedlander synthesis .................................................................................................157
Table 7.5 Effect of temperature and catalyst on yield of ethyl 3- (2- ethoxy- 2- oxoacetyl)
pyrrolo [2, 1- a]isoquinoline- 2- carboxylate ................................................................162
Table 7.6 Excellent yield of pyrido[2,1- a]isoquinoline derivatives a–e ....................................163
Table 7.7 Best temperature and solvent for the preparation of
pyrrolo[2,1-α ]isoquinoline .........................................................................................164
Table 7.8 Optimization of reaction conditions under ultrasound irradiation .............................169
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