Advances in heterocyclic chemistry /

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.- Provides the latest information on heterocyclic chemistry research- Offers outstanding and original re...

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Bibliographic Details
Main Authors:	Scriven, Eric F. V. (Author), Ramsden, Christopher A. (Author)
Corporate Author:	ScienceDirect (Online service)
Format:	eBook
Language:	English
Published:	London, England : Academic Press, [2025]
Edition:	First edition.
Series:	Advances in Heterocyclic Chemistry Series.
Subjects:	Heterocyclic chemistry. Chimie des composés hétérocycliques. Electronic books.
Online Access:	Connect to the full text of this electronic book

Table of Contents:

Intro
Advances in Heterocyclic Chemistry
Copyright
Contents
Contributors
Preface
Chapter One: The chemistry and application of benzo[b]phosphole oxides
1. Introduction
2. Structure
3. Properties
3.1. General properties
3.2. Electronic properties
3.3. Molecular structures
3.4. Photophysical properties
3.4.1. Absorbance
3.4.2. Fluorescence in solution
3.4.3. Fluorescence in the solid state
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
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
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
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
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)
1. Introduction
2. Pyrrolo[1,2-b]pyridazines
2.1. Syntheses starting from pyrroles
2.2. Syntheses starting from pyridazines
2.2.1. From pyridazines and acetylenic esters
2.2.2. From hydrogenated pyridazine and cyclopropanes
2.2.3. From pyridazine and alkylidenecyclopropanes
2.2.4. From pyridazines and cyclopropenones
2.2.5. Electrooxidation of 2-substituted pyridazine
2.2.6. From pyridazines and spirocyclopropenes
2.2.7. The [3+2] cycloaddition reaction of mesoionic oxazolo[3,2-b]pyridazines
2.2.8. Intramolecular cyclization of tetrahydropyridazines
2.2.9. [3+2] Cycloaddition reaction of pyridazinium N-ylides to olefinic and acetylenic dipolarophiles
2.2.9.1. From perfluoroalkanes
2.2.9.2. From activated alkenes
2.2.9.3. From alkynes
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
4.1.1. From pyrroles.
5.7.6. Amination of pyrrolo[1,2-a]pyrazines
5.7.7. Metallation
5.7.8. Pyrrolo[1,2-a]pyrazines as dipolarophiles
5.7.9. Reaction with activated alkynes
5.7.10. Reaction with polysulfur heterocycles
5.7.11. Condensation with amines
5.7.12. Oxidation
5.8. Applications
5.9. Naturally occurring pyrrolo[1,2-a]pyrazines
5.9.1. Bicyclic 2,5-diketopiperazine alkaloids
5.9.2. Bicyclic monoketopiperazine(pyrroloketopiperazine) alkaloids
References
Chapter Four: Se NMR spectroscopy of selenium adducts of N-heterocyclic carbenes
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. P NMR spectroscopy of carbene-phosphinidene adducts
2.5. JC,Se coupling constants
2.6. Additional methods for the characterization of electronic properties of NHCs
3. The characterization of NHCs by means of Se NMR spectroscopy
3.1. General aspects
3.2. The influence of the referencing method
3.3. Solvent effects on Se NMR resonance frequencies of NHC-selenium adducts
3.4. Influence of the concentration of the solute on the Se NMR chemical shifts
3.5. Temperature dependence of Se NMR chemical shifts
3.6. Dependence of the Se NMR shifts on the pH value
3.7. Substituent effects on the Se NMR resonance frequencies
3.7.1. Sterically demanding substituents
3.7.2. Conjugation
3.7.3. Cationic N-heterocyclic carbenes
3.7.4. Anionic N-heterocyclic carbenes
4. Se NMR resonance frequencies of selenoethers and selenenyls
5. Conclusion
6. Tabular compilation of spectroscopic data of selenones of N-heterocyclic carbenes
References
Index.