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Advances in Heterocyclic Chemistry, Volume 127, the latest release in this definitive series in the field highlights the areas where biology and organic chemistry increasingly intersect. This updated volume includes chapters on The Pictet-Spengler Reaction (1990-2017): A Powerful Strategy for the Synthesis of Heterocycles, Organometallic Complexes of Polyazines, Recent Developments in the Chemistry of Boron- dipyrromethene (BODIPY) Fluorescent Dyes and their Aza analogues, Reactions of 3-Pyrrolin-2-ones, Arsole, Stibole, Bismole, and fused systems , The Chemistry of Dihydrothienopyrrolones, the Application of the Baylis-Hillman Reaction in Heterocyclic Chemistry, and 5-Endo Cyclisation, amongst other topics.- Presents the definitive serial in the field of heterocyclic chemistry- Serves as the go-to reference for organic chemists, polymer chemists and many biological scientists- Provides comprehensive reviews written by established authorities in the field- Combines descriptive synthetic chemistry and mechanistic insights to enhance our understanding on how chemistry drives the preparation and useful properties of heterocyclic compounds.
Front Cover; Advances in Heterocyclic Chemistry; Copyright; Contents; Contributors; Preface; Chapter One: Recent advances in 1,2,4-triazolo[1,5-a]pyrimidine chemistry; 1. Introduction; 1.1. General survey; 1.2. Scope and limitation; 1.3. Nomenclature; 2. Occurrence and synthesis; 2.1. Survey; 2.2. Occurrence; 2.3. Syntheses from 5-amino-1,2,4-triazoles and 1,3-biselectrophiles; 2.3.1. Principle and conditions; 2.3.2. The diversity of biselectrophiles; 2.3.3. Regioselectivity; 2.3.4. The direct synthesis of triazolopyrimidines substituted onto carbon ring atoms
2.3.5. The use of modified biselectrophiles2.3.6. The use of polyfunctional electrophiles; 2.3.7. Syntheses via dihydro triazolopyrimidines; 2.3.8. Multicomponent reactions; 2.3.9. Special syntheses; 2.4. Syntheses using special aminotriazole derivatives; 2.4.1. Syntheses of N-substituted triazolopyrimidines; 2.4.2. The use of aminotriazole-based intermediates; 2.5. Triazole ring syntheses; 2.5.1. Syntheses from 1,2-diaminopyrimidines; 2.5.2. Syntheses from N-(pyrimid-2-yl)amidine-series compounds; 2.5.3. Syntheses from 2-hydrazinopyrimidines; 2.5.4. Other triazole ring syntheses
2.6. Other routes to triazolopyrimidines2.6.1. Aromatization of dihydro derivatives; 2.6.2. Ring transformation and cleavage; 3. Structure; 3.1. Theoretical methods; 3.2. X-ray diffraction; 3.3. Molecular spectra; 3.3.1. H NMR spectra; 3.3.2. C NMR spectra; 3.3.3. F NMR spectra; 3.3.4. Electronic spectra; 3.3.5. Infrared and Raman spectra; 3.3.6. Mass spectra; 3.4. Physicochemical properties; 3.5. Tautomerism; 4. Reactivity; 4.1. Triazolopyrimidines as bases and acids; 4.1.1. Protonation and dissociation; 4.1.2. Coordination; 4.2. Alkylation at nitrogen ring atoms
4.3. Carbon-carbon coupling at ring atoms4.3.1. The use of organometallic and metal salt reagents; 4.3.2. Suzuki coupling; 4.3.3. Sonogashira coupling; 4.3.4. Oxidative coupling; 4.3.5. Reductive coupling; 4.3.6. Nucleophilic addition; 4.4. Other reactions at ring atoms; 4.5. Nucleophilic substitution of functional groups at the rings; 4.5.1. Substitution of halogen; 4.5.2. Substitution of oxygen-, sulfur-, or nitrogen-containing functions; 4.6. Transformation of individual substituents; 4.6.1. Oxygen- or sulfur-containing groups; 4.6.2. Amines and their derivatives
4.6.3. Carbonyl containing groups4.7. Ring cleavage and recyclization; 4.8. Anellation of heterocyclic rings; 4.8.1. Anellation onto 6/7 positions; 4.8.2. Anellation onto other positions; 4.9. Reactivity of side chains; 4.9.1. Reactions involving halogen or oxygen functionalities; 4.9.2. Reactions involving sulfur, nitrogen, or phosphorus functionalities; 4.9.3. Formation of hydrocarbon groups; 4.9.4. Formation of diheterocyclyl compounds; 5. Application; 5.1. Pharmaceutical use; 5.2. Agrochemical use; 5.3. Optical and information recording uses; 5.4. Other uses; References
Includes bibliographical references and index.
Advances in heterocyclic chemistry. Volume 127
[Place of publication not identified] : Elsevier Academic Press, 2019
Advances in Heterocyclic Chemistry ; v. 127