Download Chemistry of Heterocyclic Compounds: Quinolines, Part I, PDF

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

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Read or Download Chemistry of Heterocyclic Compounds: Quinolines, Part I, Volume 32 PDF

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Originally reportedaz4as giving a 2-aminoquinoline (64; 38 The Physical and Chemical Properties of Quinoline &Hg& I I SKCH,), Si(CH,), I R1= R2= H) it was subsequently noted62s that the products included 4-amino- quinoline (65); the reagent was sodium amide in boiling toluene. Another minor product was a dihydroquinoline, oxidized to 2,3'-biquinoline (66). 626 Hydrogen was collected during the reaction and Bergstrom suggested that the initial addition product (67) lost hydrogen to give the anion (68).

After reaction at higher temperatures (70 "C) the C0,R-free triazoloquinolinium salt (52) could be isolated after addition of perchloric acid to the reaction mixture; reaction at still higher temperatures (160 "C) gave the cyanamide (53), either directly from quinoline and tert-butyihydrazonochloroacetate or from compound (52) by treatment with more quinoline. 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.

The reaction between quinoline and an alkyl- or aryl-lithium reagent, or between quinoline and a Grignard reagent, have been referred to previously (p. 30). The majority of reactions between quinoline and organometallic reagents of these types appear to give 2-substituted quinolines and fall within the scope of this section. Thus 2-phenylquinoline is obtained from quinoline with phenylsodiumsl1 (67%), phenyl- ~ l ~ The reaction lithiUm554,612, 613 (85%), or phenylmagnesium b r ~ m i d e , ~ l * (66%).

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