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Synthesis using Vilsmeier reagents

Author: Charles M Marson; Paul R Giles
Publisher: Boca Raton : CRC Press, Taylor & Francis Group, 2018.
Series: CRC revivals.
Edition/Format:   eBook : Document : EnglishView all editions and formats
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Genre/Form: Electronic books
Additional Physical Format: Print version:
Marson, C.M.
Synthesis Using Vilsmeier Reagents
Milton : CRC Press,c2018
Material Type: Document, Internet resource
Document Type: Internet Resource, Computer File
All Authors / Contributors: Charles M Marson; Paul R Giles
ISBN: 9781351085526 1351085522 9781351077071 1351077074
OCLC Number: 1020699948
Notes: "First published 1994 by CRC Press"--Copyright page.
Description: 1 online resource (251 pages) : illustrations.
Contents: Cover --
Title Page --
Copyright Page --
Preface --
Table of Contents --
1 Formation, Structure, and General Reactions of Vilsmeier Reagents --
1.1 Introduction --
1.2 Formation and Structure of Halomethyleneiminium Salts (Vilsmeier Reagents) --
1.2.1 Physical Properties of Vilsmeier Reagents --
1.2.2 Outline of the Formation of Vilsmeier Salts --
1.2.3 DMF-POC13 and Related Adducts --
1.2.4 Higher Amide-POC13 Adducts --
1.2.5 Thioamide-POC13 and Related Adducts --
1.2.6 Acid Amide-Pyrophosphoryl Chloride Adducts --
1.2.7 Acid Amide-Carbonyl Halide Adducts --
1.2.8 Acid Amide-Phosphorus Trihalide Adducts --
1.2.9 Acid Amide-Thionyl Chloride Adducts --
1.2.10 Acid Amide-Sulfuryl Chloride Adducts --
1.2.11 Acid Amide-Carboxylic Acid Adducts --
1.2.12 Acid Amide-Acid Anhydride Adducts --
1.3 General Reactions of Halomethyleneiminium Salts --
1.3.1 Introduction --
1.3.2 Electrophilicity of Halomethyleneiminium Salts and Selection of the Vilsmeier Reagent --
1.3.3 Substitution of Aromatic and Heteroaromatic C-H Bonds --
1.3.4 Reactions of Alkenic Double Bonds --
1.3.5 Reactions of Ketones --
1.3.6 Reactions of Amidic Carbonyl Compounds --
References --
2 Synthesis of Functional Groups using Vilsmeier Reagents --
2.1 Bromo Compounds --
2.1.1 Alkyl Bromides --
2.1.2 Vinyl Bromides --
2.1.3 Heteroaryl Bromides --
2.2 CNoro Compounds --
2.2.1 Alkyl Chlorides, including Chloromethyl Compounds --
2.2.2 Vinyl Chlorides --
2.2.3 Aryl Chlorides --
2.2.4 Heteroaryl Chlorides --
2.3 Akynes --
2.4 Ethers --
2.5 Dialkylaminomethyl Compounds --
2.6 Î -Dialkylaminornethylene Compounds --
2.6.1 Î -Dialkylarninomethylene Heterocycles --
2.6.2 Î -Dialkylaminomethylene Lactams --
2.7 Epoxides --
2.8 Aldehydes --
2.8.1 Aliphatic Aldehydes --
2.8.2 Π,β-Unsaturated Aldehydes --
2.8.2.1 Π,β-Unsaturated Aldehydes with no Functional Group at the β-Position. 2.8.2.2 β-Hydroxy and β-Alkoxy Π,β-Unsaturated Aldehydes --
2.8.2.3 Π,β-Unsaturated Aldehydes with other Functional Groups at the β-Position --
2.8.2.4 Π,β-Unsaturated Aldehydes with a β-amino Group (Vinylogous Formamides) --
2.8.2.5 Other Vinylogous Formamides --
2.8.3 Aliphatic Thioaldehydes --
2.8.4 Aromatic Aldehydes --
2.8.5 Heterocyclic Aldehydes --
2.8.5.1 Indoles, Pyrroles and Porphyrins --
2.8.5.2 Furans and Thiophenes --
2.8.5.3 Pyridines --
2.8.5.4 Pyrimidine Derivatives (including Barbituric Acid) --
2.8.5.5 Miscellaneous --
2.8.6 Heterocyclic Thioaldehydes --
2.9 Ketones --
2.9.1 2-Chloroketones --
2.9.2 β-Amino-Π,β-Unsaturated Ketones --
2.10 Other Π,β-Unsaturated Carbonyl Compounds --
2.11 β-Halovinylaldehydes --
2.11.1 Formation of β-Halovinylaldehydes --
2.11.2 β-Bromovinylaldehydes --
2.11.3 β-Chlorovinylaldehydes --
2.11.3.1 Introduction --
2.11.3.2 β-Chlorovinylaldehydes from Alkyl Aryl Ketones --
2.11.3.3 β-Chlorovinylaldehydes from Saturated Monocarbocyclic Ketones --
2.11.3.4 β-Chlorovinylaldehydes from Π,β-Unsaturated Carbocyclic Ketones --
2.11.3.5 β-Chlorovinylaldehydes from Benzo-fused Cycloalkanones --
2.11.3.6 β-Chlorovinylaldehydes from Cycloalkanones --
2.11.3.6 β-Chlorovinylaldehydes from Cycloalkanones fused to Heteroaromatic Rings --
2.11.3.7 β-Chlorovinylaldehydes from Cyclic Ketones with One or More Heteroatoms in the Ring --
2.11.3.8 β-Chlorovinylaldehydes from Polycyclic Systems --
2.11.3.9 β-Chlorovinylaldehydes in Synthesis --
2.11.4 β-Iodovinylaldehydes --
2.12 β-Halovinylketones --
2.13 Carboxylic Acids --
2.14 Carboxylic Acid Halides and Sulfonyl Chlorides --
2.14.1 Carboxylic Acid Bromides --
2.14.2 Carboxy lic Acid Chlorides --
2.14.3 Carboxylic Acid Fluorides --
2.14.4 Sulfonyl Chlorides --
2.15 Anhydrides --
2.16 Carbamates, Carbamoyl Halides, and Isocyanates. 2.17 Carbodiimides --
2.18 Thiocyanates --
2.19 Esters and Derivatives --
2.19.1 Formates and Higher Esters --
2.19.2 1-Acyloxy-2-chloroalkanes --
2.19.3 Thioesters and Dithioesters --
2.19.4 p-Amino-Π,β-Unsaturated Esters --
2.19.5 Phosphate Esters --
2.19.6 Orthoesters --
2.20 Amides and Derivatives --
2.20.1 Formamides --
2.20.2 Thioamides --
2.20.3 Amide Acetals --
2.20.4 Amide Mercaptals --
2.20.5 Î -Chloroamides and Î ,Î -Dichloroamides --
2.20.6 β-Ketocarboxylic Acid Amides --
2.20.7 Π,β-Unsaturated Amides --
2.20.8 Urea --
2.20.9 Peptides and Nucleotides --
2.21 Enamines --
2.21.1 Î -Chloroenamines --
2.21.2 Î -Cyanoenamines --
2.21.3 N-Formylenamines --
2.21.4 Cyclic Enamines --
2.22 Ynamines --
2.23 Nitriles --
2.24 Isocyanides --
2.25 Isocyanide Dichlorides --
2.26 Viny logous Amides --
2.27 Amidines and Derivatives --
2.27.1 Amidines and Acyclic Amide --
2.27.2 Amidines from Lactarns --
2.27.3 Vinylogous Amidines --
2.28 Amidrazones --
2.29 Iminium Salts --
2.29.1 General (including Gold's Reagent) --
2.29.2 Amidinium Salts --
2.29.3 1,5-Diazapentadienium Salts (Vinarnidinium or Trimethinium Salts) --
2.29.4 Pentamethinium Salts --
2.29.5 Polymethinium Salts --
Reference --
3 Formation of Rings by Aromatization and Heteroaromatization --
3.1 Ring Formation by Aromatization --
3.1.1 Derivatives of Benzene --
3.1.2 Derivatives of Benzo-fused Cycloalkanes --
3.1.3 Derivatives of Naphthalene --
3.1.4 Derivatives of Anthracene --
3.1.5 Derivatives of Carbazoles --
3.2 Ring Formation by Heteroaromatization --
3.2.1 Furans --
3.2.2 Thiophenes --
3.2.3 Pyrroles --
3.2.4 Pyrazoles --
3.2.5 Indoles --
3.2.6 Pyrimidines --
3.2.7 Isoquinolines --
3.2.8 Miscellaneous Ring Systems --
Reference --
4 Ring Formation using either Vilsmeier Reagents or β-Chlorovinylaldehydes --
4.1 Non-benzenoid Carbocyclic Systems --
4.1.1 Cyclopentenes. 4.1.2 Fulvenes --
4.1.3 Fused Ring Systems --
4.2 Benzenoid Ring Systems --
4.2.1 Benzene Rings --
4.2.2 Indenes and Benzofulvenes --
4.2.3 Dihydronaphthalenes --
4.2.4 Dithienobenzenes --
4.3 Synthesis of Non-Aromatic Heterocycles --
4.3.1 Pyrans, Pyrones, and their Derivatives --
4.3.2 Thiopyrans, Thiopyranones and their Derivatives --
4.3.3 Quinolinones and Isoquinolinones --
4.3.4 Quinolizinones --
4.3.5 Pyrrolines --
4.3.6 Miscellaneous Ring Systems --
4.4 Synthesis of Heteroaromatic Systems --
4.4.1 Compounds containing a Five-Membered Ring --
4.4.1.1 Furans and Benzsfurans --
4.4.1.2 Pyrroles --
4.4.1.3 Indoles --
4.4.1.4 Thiophenes and Benzothiophenes --
4.4.1.5 Oxazoles and Benzoxazoles --
4.4.1.6 Isoxazoles --
4.4.1.7 Pyrazoles --
4.4.1.8 Benzimidazoles --
4.4.1.9 Isothiazoles --
4.4.1.10 Pyrrolopyrazines, Pyrrolopyridines and Pyyroloquinoline --
4.4.1.11 Miscellaneous --
4.4.2 Compounds containing a Six-Membered Ring --
4.4.2.1 Pyrylium and Thiopyrylium Salts --
4.4.2.2 Benzopyrones and Naphthopyrones --
4.4.2.3 Pyridines --
4.4.2.4 Pyrdinium Salts --
4.4.2.5 Quinolines --
4.4.2.6 Quinolinium Salts --
4.4.2.7 Quinolizinium Salts --
4.4.2.8 Isoquinolines --
4.4.2.9 Pyrimidines --
4.4.2.10 1,3-Thiazinium Salts --
4.4.2.11 Adenine --
4.4.2.12 Naphthyridines --
4.4.2.13 Pyrimidoindoles --
4.4.2.14 Pyrimidobenzodiazepines --
4.4.2.15 Miscellaneous --
4.5 Formation of Seven-Membered Rings --
4.5.1 2-Azaazulenes --
4.5.2 Benzodiazepines --
4.5.3 Benzoxazolodiazepines --
4.5.4 Thiazepines and Benzothiazepines --
References --
5 Transformations to give New Ring Systems --
References --
Index.
Series Title: CRC revivals.
Responsibility: Charles M. Marson, Department of Chemistry, University of Sheffield, United Kingdom, Paul R. Giles, Department of Organic Chemistry, Catholic University of Louvain, Belgium.

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