Advances in Heterocyclic Chemistry

1st Edition, Volume 145 - February 14, 2025
Imprint: Academic Press
Editors: Eric F.V. Scriven, Christopher A. Ramsden
Language: English
Hardback ISBN:
9 7 8 - 0 - 4 4 3 - 3 1 6 6 0 - 9
eBook ISBN:
9 7 8 - 0 - 4 4 3 - 3 1 6 6 1 - 6

Advances in Heterocyclic Chemistry series, highlights new advances in the field, with this new volume presenting interesting chapters. Each chapter is written by an intern… Read more

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Advances in Heterocyclic Chemistry series, highlights new advances in the field, with this new volume presenting interesting chapters. Each chapter is written by an international board of authors.

Advances in Heterocyclic Chemistry, 145
Cover image
Title page
Table of Contents
Series Page
Copyright
Contributors
Preface
Chapter One The chemistry and application of benzo[b]phosphole oxides
Abstract
Keywords
1 Introduction
2 Structure
3 Properties
3.1 General properties
3.2 Electronic properties
3.3 Molecular structures
3.4 Photophysical properties
3.5 Electrochemical properties
3.6 Photochromism
4 Synthetic approaches to 2,3-disubstituted benzo[b]phosphole oxides
4.1 [4 + 1] Cycloaddition
4.2 Intramolecular cyclization
4.3 [3 + 2] Approaches
4.4 One-pot multicomponent reaction using organometallic reagents
4.5 Direct ortho-alkenylation and cyclization of arylthiophoshinamides
4.6 Catalytic cross-coupling reactions
4.7 C—H bond activation reactions
4.8 Radical addition/cyclization
4.9 Other methods
5 Synthesis of 2-substituted benzo[b]phosphole oxides
5.1 Intramolecular cyclization
5.2 Catalytic cross-coupling reactions
5.3 Other methods
6 Synthesis of 3-arylbenzo[b]phosphole oxides
6.1 Suzuki-Miyaura cross-coupling
6.2 Double C—P bond formation
6.3 Cu-mediated intramolecular cyclization
7 Synthesis of 1-phenylbenzo[b]phosphole oxide
7.1 Diels-Alder reactions
7.2 Phospha-Friedel-Crafts cyclization
7.3 [4 + 1] Approaches
7.4 Ring-closing metathesis (RCM)
7.5 2-Silyl group removal
7.6 Ag-promoted radical cycloisomerization
8 Reactivity of benzo[b]phosphole oxides
8.1 Functionalization at the phosphorus atom
8.2 Halogenation
8.3 C—H bond activation
8.4 Friedel-Crafts reaction
8.5 Ring-closing metathesis (RCM)
8.6 Ring opening
8.7 Cycloaddition reactions
8.8 Other reactions
9 Applications
9.1 Fluorescent dyes
9.2 Optoelectronic and photovoltaic devices
9.3 Synthesis of metal complexes
9.4 Synthesis of polymers
9.5 Ligands in asymmetric synthesis
10 Conclusions
Acknowledgments
References
Chapter Two The Thorpe-Ziegler reaction: A powerful strategy for the synthesis of heterocycles
Abstract
Keywords
1 Introduction
2 The Thorpe-Ziegler Reaction
2.1 Synthesis of five-membered heterocycles
2.2 Synthesis of six-membered heterocycles
2.3 Synthesis of seven-membered heterocycles
3 Conclusion
Acknowledgment
References
Chapter Three N-Bridgehead pyrrolodiazines (1998–2023)
Abstract
Keywords
1 Introduction
2 Pyrrolo[1,2-b]pyridazines
2.1 Syntheses starting from pyrroles
2.2 Syntheses starting from pyridazines
2.3 Miscellaneous pyrrolo[1,2-b]pyridazine syntheses
2.4 Applications
3 Pyrrolo[1,2-a]pyrimidines
3.1 Syntheses from pyrroles
3.2 Syntheses from pyrimidines
3.3 Syntheses from heterocyclic ketene aminals
3.4 Retro Diels-Alder reaction
3.5 Miscellaneous syntheses
3.6 Naturally occurring pyrrolo[1,2-a]pyrimidines
3.7 Applications
4 Pyrrolo[1,2-c]pyrimidines
4.1 Syntheses from pyrroles
4.2 Syntheses from pyrimidines
4.3 Syntheses from acyclic compounds
4.4 Naturally occurring pyrrolo[1,2-c]pyrimidines
5 Pyrrolo[1,2-a]pyrazines
5.1 From pyrazines
5.2 From pyrroles and hydrogenated pyrroles
5.3 By multicomponent reactions (MCRs)
5.4 By multicomponent Ugi reaction
5.5 From heterocycles other than pyrazines and pyrroles
5.6 By double cyclization of acyclic compounds
5.7 Functionalization
5.8 Applications
5.9 Naturally occurring pyrrolo[1,2-a]pyrazines
References
Chapter Four 77Se NMR spectroscopy of selenium adducts of N-heterocyclic carbenes
Abstract
Keywords
1 Introduction
2 Overview of probes for characterization of electronic properties of NHCs
2.1 Tolman electronic parameter (TEP)
2.2 Huynh electronic parameter (HEP)
2.3 Carbene relative energy of formation (CREF)
2.4 31P NMR spectroscopy of carbene-phosphinidene adducts
2.5 1JC,H and 1JC,Se coupling constants
2.6 Additional methods for the characterization of electronic properties of NHCs
3 The characterization of NHCs by means of 77Se NMR spectroscopy
3.1 General aspects
3.2 The influence of the referencing method
3.3 Solvent effects on 77Se NMR resonance frequencies of NHC-selenium adducts
3.4 Influence of the concentration of the solute on the 77Se NMR chemical shifts
3.5 Temperature dependence of 77Se NMR chemical shifts
3.6 Dependence of the 77Se NMR shifts on the pH value
3.7 Substituent effects on the 77Se NMR resonance frequencies
4 77Se NMR resonance frequencies of selenoethers and selenenyls
5 Conclusion
6 Tabular compilation of spectroscopic data of selenones of N-heterocyclic carbenes
References
Index

Eric F.V. Scriven

Eric Scriven was educated in the UK and appointed lecturer in organic chemistry at the University of Salford in 1971. He joined Reilly Industries in 1979, and was Head of Research & Development 1991-2003. He is now Publishing Editor of Arkivoc and is based at the Department of Chemistry, University of Florida in Gainesville. His research interests are in heterocyclic chemistry, especially pyridines. He has over 100 publications and patents in heterocyclic chemistry. He has also published and consulted in the field of technology management. He was a founding editor (with Hans Suschitzky) of Progress in Heterocyclic Chemistry now in its 25th year. He has collaborated with Alan Katritzky and others as an Editor-in-Chief of Comprehensive Heterocyclic Chemistry 2nd and 3rd editions. He has edited two other works, Azides and Nitrenes (1984), and Pyridines (2013).

Affiliations and expertise

Publishing Editor of Arkivoc, Department of Chemistry, University of Florida, Gainesville, USA

Christopher A. Ramsden

Chris Ramsden was born in Manchester, UK in 1946. He is a graduate of Sheffield University and received his PhD in 1970 for a thesis entitled ‘Meso-ionic Compounds’ (W. D. Ollis) and a DSc in 1990. Subsequently he was a Robert A. Welch Postdoctoral Fellow at the University of Texas (with M. J. S. Dewar)(1971-3), working on the development and application of semi-empirical MO methods, and an ICI Postdoctoral Fellow at the University of East Anglia (with A. R. Katritzky)(1973-6), working on the synthesis of novel heterocycles. In 1976 he moved to the pharmaceutical industry and was Head of Medicinal Chemistry (1986-1992) at Rhone-Poulenc, London. He moved to Keele University as Professor of Organic Chemistry in 1992, where he is now Emeritus Professor. His research interests include the structure and preparation of novel heterocycles, three-centre bonding in the context of the chemistry of betaines and hypervalent species, and the properties of the enzyme tyrosinase and related ortho-quinone chemistry. He was an Editor-in-Chief of ‘Comprehensive Heterocyclic Chemistry III’ and a co-author of ‘The Handbook of Heterocyclic Chemistry, 3rd Edn, 2010.

Affiliations and expertise

Professor of Organic Chemistry, Keele University, Staffordshire, UK

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