By A. Mustafa
Chapter I Benzofurans (pages 1–77):
Chapter II Acylbenzofurans (pages 78–110):
Chapter III Benzofurancarboxylic Acids (pages 111–142):
Chapter IV Hydrogenated Benzofurans (pages 143–209):
Chapter V Benzofuranones (pages 210–296):
Chapter VI clearly happening Benzofurans (pages 297–369):
Chapter VII obviously happening Spirobenzofuranones (pages 370–430):
Chapter VIII much less universal and changed certainly taking place Benzofurans (pages 457–462):
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Extra info for Chemistry of Heterocyclic Compounds: Benzofurans, Volume 29
5 y Whalley and Lloyd"" have shown that. ' 6' attempts to prepare 2,4,6-trimethoxyphenylacetyl chloride through action of phosphorus pentachloride on the appropriate acid resulted in the formation of an anamolous acid chloride. 6-trimethoxybenzyl)-6-methoxybenzofuran (151) and several derivatives there of Eq. 16' 0 OMe I 7 i -OMc The ketonitrile (152) has been evaluated as a convenient route for the synthesis of benzofuranol methyl ethers as outlined in Eq. N 152 Me0 41 I H2 Periodic oxidation of melacacidin tetramethyl ether has been shown to give 2-(3,4-dimethoxyphenyl)-6,7-dimethoxybenzofuran(153).
L 4 The ultraviolet spectra of 4- and 6-chlorobenzofuran-2-carboxylic acid exhibit enhanced bathochromic effects which are caused by chlorine where conjugation with a carbonyl group is possible. B. Bromo Derivatives Bromination of benzofuran was reported to give the unstable 2,3-dibromobenzofurdn. I ' I ' However 2-methyl- and 2-phenylbenzofuran gave the corresponding 3-bromo derivatives. "' However Smith"' found that 2-benzofurancarboxylic acid did not undergo bromination; its ethyl ester yielded the 5-bromo derivative.
Which is less nucleophilic than phenyldiethylaminoacetylene. 4addition) (Eq. 5 I ). '*" Reaction of 165 with Grignard reagents resulted in the formation of the corresponding tertiary carbinols (167). which upon treatment with p l y phosphoric acid afforded 3-phenyl-2-dialkylaminodihydrobenzofurans (168) (Eq. 5 2 ) . '"' The generalized Leuckart reaction with formylated derivatives of primary and secondary amines produces less resinous products than when formamide is used and results in formation of N-substituted derivatives.
Chemistry of Heterocyclic Compounds: Benzofurans, Volume 29 by A. Mustafa