The Chemistry of Heterocyclic Compounds, Benzofurans

The Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects - properties, synthesis, reactions, physiological and industrial significance - of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.

Autorentext
Ahmed Mustafa is the author of Benzofurans, Volume 29, published by Wiley.

Zusammenfassung
The Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects properties, synthesis, reactions, physiological and industrial significance of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.

Inhalt
I. Benzofurans 1 1. Introduction and Nomenclature 1 2. Benzofuran and Its Alkyl Derivatives 2 A. Preparation 2 a. Catalytic Dehydrocyclization 2 b. Cyclization of Allyphenols 2 c. Cyclodehydration of Aryloxy ketones 3 d. Rearrangement of O-Aryloximes 5 e. Dehydrogenation of Bz- AIkyldihydrohenzofurans 6 f. Reduction of 2-Acetonyl-o-benzoquinols 7 g. Hydrogenation of 2-Acetylhenzofuran 8 h. Reaction of Copper Acetylides with Aryl Halides 8 i. Decarboxylation of Benzofurancarboxylic Acids 9 j. Photochemical Formation of Benzofurans 9 k. Adsorptive Cyclization 11 l. Condensation of Methylene Bis (ethyl sulfone) with Salicylaldehydes 12 3. Aryl benzofurans 13 A. Preparation 13 a. Cvdodehydration of io-Arloxyacelophenones 13 b. Condensation of Benzoins with Phenols 19 c. f ,3-Dipolar Additions of Oxocarbenes 20 d. Copper-Catalyzed Decomposition of Diazoketones 21 e. Ethynation of P-Benzoquinone 21 f Oxidation of Flavylium and Pyrylium Salts 22 g. Algar-Flynn-Oyamada Oxidation of 2'-Hydroxy- chalcones 24 h. Acid-Catalyzed Cyclization of O-Aryloximes 24 i. Photolytic Cyclizations 25 j. Miscellaneous 25 4. Halobenzofurans 28 A. Chloro Derivatives 28 B. Bromo Derivatives 28 C. Iodo Derivatives 29 D. Fluoro Derivatives 29 5. Nitrobenzofurans 33 6. Benzofuranols 34 7. Aminobenzofurans 42 8. Benzofuranq uinones 53 9. Miscellaneous Reactions and Properties 56 A. Catalytic Hydrogenation 56 B. Oxidation 59 C. Ozonolysis 60 D. Nitration 62 E. Halogenation 62 F. Benzofuranylmetallic Compounds 63 G. Friedel-Crafts Techniques 65 H. Hoesch and Gatterman Techniques 67 I. With Diazoalkanes 67 J. With Dihalocarbene 68 K. Cyclophotochemical Addition 68 L. Polymerization 69 M. Miscellaneous Reactions 69 References 70 II. Acylbenzofurans 78 1. Formylbenzofurans 2. Acylbenzofurans 3. Miscellaneous reactions A. Reduction 89 B. Oxidation 89 C. Alkaline Degradation 90 D Rearrangement of Acylbenzofuran Oximes 97 E. Rearrangement (Migration) in Acylbenzofurans 101 F. Willgerodt-Kindler Reaction 102 G. Wittig Reaction 102 H. Miscellaneous 104 References III. Benzofurancarboxylic acids 111 1. Benzofuran monocarboxylic Acids 111 A. 2-Benzofurancarboxylic Acids 111 B. 3-Benzofurancarboxylic Acids 114 C. Hydroxybenzofurancarboxylic Acids 117 2. Benzofuran Dicarboxylic Acids 120 3. Benzofuranylalkanoic Acids 124 A. Benzofuranylacetic Acids 124 B. Benzofuranylpropionic Acids 126 C. Benzofuranylbutyric Acids 128 D. Miscellaneous Benzofuranylalkanoic Acids 130 A. Halogenation 132 B. Chloromethylation 132 C. Nitration 132 D. Saponification 135 E. Catalytic Hydrogenation 135 F. Peroxide Formation and Ozonolysis 135 G. Acylation 138 H. Alkylation 139 I. Miscellaneous Reactions 139 References IV. Hydrogenated Benzofurans 143 1. Dihydrobenzofurans 143 A. Alkyl- (or Aryl-) Substituted 2,3- Dihydrobenzofurans 143 B. Halogen-Substituted 2,3-Dihydrobenzofurans 155 C. Nitro-Substituted 2,3-Dihydrobenzofurans 157 D. Amino-Substituted 2,3-Dihydrobenzofurans 161 E. 2,3-Dihydrobenzofuranols 165 F. Geometrical Isomers of 2,3- Dihydrobenzofurans 181 G. Miscellaneous Reactions of 2,3- Dihydrobenzofurans 186&l...

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