Benzofurans, Volume 29

Inbunden, Engelska, 2007

Del 25 i serien Chemistry of Heterocyclic Compounds: A Series of Monographs

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Beskrivning

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.

Produktinformation

Utgivningsdatum:2007-07-17
Mått:157 x 235 x 36 mm
Vikt:822 g
Format:Inbunden
Språk:Engelska
Serie:Chemistry of Heterocyclic Compounds: A Series of Monographs
Antal sidor:514
Upplaga:74099
Förlag:John Wiley & Sons Inc
ISBN:9780471382072

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Ahmed Mustafa, Chemistry Department, Cairo University.

Innehållsförteckning

I. Benzofurans 11. Introduction and Nomenclature 12. Benzofuran and Its Alkyl Derivatives 2A. Preparation 2a. Catalytic Dehydrocyclization 2b. Cyclization of Allyphenols 2c. Cyclodehydration of Aryloxy ketones 3d. Rearrangement of O-Aryloximes 5e. Dehydrogenation of Bz- AIkyldihydrohenzofurans 6f. Reduction of 2-Acetonyl-o-benzoquinols 7g. Hydrogenation of 2-Acetylhenzofuran 8h. Reaction of Copper Acetylides with Aryl Halides 8i. Decarboxylation of Benzofurancarboxylic Acids 9j. Photochemical Formation of Benzofurans 9k. Adsorptive Cyclization 11l. Condensation of Methylene Bis (ethyl sulfone) with Salicylaldehydes 123. Aryl benzofurans 13A. Preparation 13a. Cvdodehydration of io-Arloxyacelophenones 13b. Condensation of Benzoins with Phenols 19c. f ,3-Dipolar Additions of Oxocarbenes 20d. Copper-Catalyzed Decomposition of Diazoketones 21e. Ethynation of P-Benzoquinone 21f Oxidation of Flavylium and Pyrylium Salts 22 g. Algar-Flynn-Oyamada Oxidation of 2'-Hydroxy- chalcones 24h. Acid-Catalyzed Cyclization of O-Aryloximes 24i. Photolytic Cyclizations 25j. Miscellaneous 254. Halobenzofurans 28A. Chloro Derivatives 28B. Bromo Derivatives 28C. Iodo Derivatives 29D. Fluoro Derivatives 295. Nitrobenzofurans 336. Benzofuranols 347. Aminobenzofurans 428. Benzofuranq uinones 539. Miscellaneous Reactions and Properties 56A. Catalytic Hydrogenation 56B. Oxidation 59C. Ozonolysis 60D. Nitration 62E. Halogenation 62F. Benzofuranylmetallic Compounds 63G. Friedel-Crafts Techniques 65H. Hoesch and Gatterman Techniques 67I. With Diazoalkanes 67J. With Dihalocarbene 68K. Cyclophotochemical Addition 68L. Polymerization 69M. Miscellaneous Reactions 69References 70II. Acylbenzofurans 781. Formylbenzofurans2. Acylbenzofurans3. Miscellaneous reactionsA. Reduction 89B. Oxidation 89C. Alkaline Degradation 90D Rearrangement of Acylbenzofuran Oximes 97E. Rearrangement (Migration) in Acylbenzofurans 101F. Willgerodt-Kindler Reaction 102G. Wittig Reaction 102H. Miscellaneous 104ReferencesIII. Benzofurancarboxylic acids 1111. Benzofuran monocarboxylic Acids 111A. 2-Benzofurancarboxylic Acids 111B. 3-Benzofurancarboxylic Acids 114C. Hydroxybenzofurancarboxylic Acids 1172. Benzofuran Dicarboxylic Acids 1203. Benzofuranylalkanoic Acids 124A. Benzofuranylacetic Acids 124B. Benzofuranylpropionic Acids 126C. Benzofuranylbutyric Acids 128D. Miscellaneous Benzofuranylalkanoic Acids 130A. Halogenation 132B. Chloromethylation 132C. Nitration 132D. Saponification 135E. Catalytic Hydrogenation 135F. Peroxide Formation and Ozonolysis 135G. Acylation 138H. Alkylation 139I. Miscellaneous Reactions 139ReferencesIV. Hydrogenated Benzofurans 1431. Dihydrobenzofurans 143A. Alkyl- (or Aryl-) Substituted 2,3- Dihydrobenzofurans 143B. Halogen-Substituted 2,3-Dihydrobenzofurans 155C. Nitro-Substituted 2,3-Dihydrobenzofurans 157D. Amino-Substituted 2,3-Dihydrobenzofurans 161E. 2,3-Dihydrobenzofuranols 165F. Geometrical Isomers of 2,3- Dihydrobenzofurans 181G. Miscellaneous Reactions of 2,3- Dihydrobenzofurans 186a. Heterocyclic Ring Opening 186b. Halogenation and Chloromethylation 188c. Acylation 188d. Dehydrogenation 190e. Mercuration 190f. Miscellaneous 1902. Bz-Dihydrobenzofurans 1923. Tetrahydrobenzofurans 1924. Hexahydrobenzofurans 1985. Octahydrobenzofurans 199References 202V. Benzofuranones 2101. 3(2H)-Benzofuranones 210A. Preparation 210B. Reactions 2202. Substituted 3(2H)-Benzofuranones 227A. 2-Hydroxy-2-benz.yl-3(2H)-Benzofuranones 227B. 2-Benzyl-3(2H)-benzofuranones 242C. 2-Acyi-3(2H)-benzofuranones 243D. Hydroxy Bz-Substituted 3(2H)-Benzofuranones 245E. Reactions of Hydroxy-Substituted 3(2H,-Benzofuranones 2463. 2(3H)-Benzofuranones 251A. Preparation 251B. Miscellaneous Reactions 2674. 2,3-Dihydrobenzofurandiones 279A. Preparation 279B. Miscellaneous Reactions 284References 289VI. Naturally Occurring Benzofurans 2971. Benzofurans 297A. 5-Methoxybenzofuran 297B. Furoventalene 297C. Euparin 299D. 5,6-Dimethoxy-2-isopropenylbenzofuran 300E. Ageratone and Dihydroageratone 300F. Pongamol 301G. Tremetone Dehydrotremetone and Hydroxytremetone 302H. 2-(6-Hydroxy-2-methoxy-3,4-methylenedioxyphenyl) benzofuran 311I. Pterofuran 312J. Eupomatene 313K. Egonol 315L. 2-(3' 4'-Dimethoxyphenyl)-5-(3"-hydroxypropyl)- 7-methoxybenzofuran 3192. 2,3-Dihydrobenzofurans 320A. Anisoxide 320B. Remirol 321C. Obtusafuran 323D. Melanoxin 323E. Hordatines A and B 3243. 2(3H)-Benzofuranones 326A. Xylerythrin 326B. Calycin 3284. 3(2H)-Benzofuranones 329A. Maesopsin 329B. Alphitonin 331C. Aurones 332a. Aureus in and Aureusidin 334b. Cernuoside 335c. Leptosin and Leptosidin 336d. Sulfuretin and Sulfurein 337e. Palasilrin 338f. Hispidol 339g- Maritimein and Maritmetin 340h. Rengasin 341i. Bracteatin and Bractein 342D. Synthetic Aurone Analogs 343E. Chemical Properties 343ReferencesVII. Naturally Occurring Spirobenzofuranones 3701. Spiro-3 (2H)-benzofuranones 370A. Griseofulvin 370a. Nomenclature 370b. Structure 371c. Synthesis of Griseofulvin and Its Analogs 379d. Dehydrogriseofulvin 385e. Dechlorogriseofulvin 388f Spirocyclic Compounds Related to Griseofulvin 390g. Detection and Estimation 416h. Biosynthesis of Griseofulvin 416i. Metabolism 418j. Biological Activities 419k. Structure—Activity Relations 420B. Geodin and Erdin 4222. Spiro-2(3H,-benzofuranones A. Picrolichenic Acid 425References 426VIII. Less Common and Modified Naturally Occurring Benzofurans 4311. Less Common Benzofurans 431A. Menthofuran 431B. Evodone 433C. Bisabolangelone 434D. Curzerenone Epicurzerenone and Isofuranogermacrene 435E. Isosericenin. Sericealacetone and Deoxysericealactone Methyl Esters 437F. ( ± )-Loliolide [( + )-Digiprolactone)] 4392. Modified Benzofurans 441A. Usnic Acid 441B. Isousnic Acid 4513. Applications of Benzofurans 452References 458Author Index 463Subject Index 491