Download e-book for iPad: Chemistry of Heterocyclic Compounds: Quinolines, Part I, by

ISBN-10: 0470187026

ISBN-13: 9780470187029

ISBN-10: 0471994375

ISBN-13: 9780471994374

Content material:
Chapter 1 The actual and Chemical houses of Quinoline (pages 1–92): Gurnos Jones
Chapter 2 Synthesis of the Quinoline Ring method (pages 93–318): Gurnos Jones
Chapter three Haloquinolines (pages 319–786): Robert okay. Smalley

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Extra resources for Chemistry of Heterocyclic Compounds: Quinolines, Part I, Volume 32

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44 a I 13; R 14; R = = R CQ2C2H5 CHQ 03 I 15 CHQ 16 Sodium amalgam in ethanol converted quinoline into 1,2,3,4-tetrahydroquinoline 548 and hydrochloric acid. During such reductions, and more prominently during reduction by zinc and ammonia545or by zinc and acetic anhydride,549,550 reduced biquinolines were also formed. The only satisfactorily characterized material was a tetrahydrobiquinoline reported by K o e n i g ~The . ~~~~ When quinoline reacts with Grignard reagents the initial product is probably always the 2-substituted 1,2-dihydroquinoline but the intermediate is very rarely isolated.

608 The yields of the triazoloquinolinium salts of type (55) were on the whole inferior to those obtained with isoquinoline; in a direct competition between quinoline and isoquinoline only the triazoloisoquinolinium salt was isolated. It is not clear whether this is a reflection of the relative steric hindrance of the nitrogen atom in quinoline, its weaker basicity, or other factors. 608 The same compound was obtained in poorer yield from diethyl malonate; the corresponding methyl ester (57; R = CH,) was obtained froin dimethyl malonate or from methyl acetoacetate.

At 450 "C the main product was 2-bromoquinoline (117) although some 3-bromoquinoline was still obtained; at 500 "C a good yield of 2-bromoquinoline (117) could be achieved, especially when the vapours were The Physical and Chemical Properties of Quinoline 48 diluted with nitrogen. Suggestions have been made that radical bromination predominates at the higher temperature. Eisch has notedBQ1 that 3-bromoquinolinium bromide can decompose at 300 "C(although it must be noted that 4-bromoquinoline and not 2-bromoquinoline is formed), and he has suggested that the differing patterns of substitution at 300 and 500 "C may indicate different stabilities of the isomers rather than differing mechanisms.

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Chemistry of Heterocyclic Compounds: Quinolines, Part I, Volume 32


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