Chemistry of Heterocyclic Compounds: Quinolines, Part III, by John V. Greenhill

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By John V. Greenhill

Quinoline Aldehydes.

Quinoline Ketones.

writer Index.

topic Index.Content:
Chapter 1 Quinoline Aldehydes (pages 1–87): John V. Greenhill
Chapter 2 Quinoline Ketones (pages 89–516): John V. Greenhill

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Extra info for Chemistry of Heterocyclic Compounds: Quinolines, Part III, Volume 32

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3 g. 4-diMe-Q, EtONO. KNH, 2-Me-Q, (HCHO),, FeSO,, tBuOOH. TFA Q, (HCHO),, FeSO,. i B u 0 0 H . hv. p. p. 6-di Ph-2-pyridone N - 82 oxide 4-Me-Q, (PhSeO),O, PhCI. 5 4-Me-Q, SeO, 64 4-Me-Q, SeO,, xylene 61 Preparation Table 3. p. ("C) 180 33 237 -2 38(d)* 181 182, 183 183b 46 179-181 32, 184 PH PIC. 8-triMe-Q-4-CH(OMe),. 4-CIC6HdCHO. p. p. p. * 72-75 Yield(%) 2-Me-4-Br-Q, BuLi; DMF 34 2-NH,-3,5-diMeC6H,COCH(OMe),, MeCOMe. EtONa 2-Me-3-NH,-Q-4-CH,OH, MnO, 85 2-CF3-4-Br-Q,BuLi; DMF 80 2,8-diCF3-4-Br-Q,B u t t DMF 63 2-CF3-4-Br-7-Me0-Q,BuLi; DMF 56 {4,6-diMe-Q-2-S),,S O , , dioxane 65 Preparation Table 3.

1 4 5 - 1 4 8 OC/l mm 4 9 , 8 3 % , b . p . p. 5%,m p 120-121 O C c R =CN, m. 3. p. ’’’ - oq. p. p. p. 265-266 OC R = 4 - 0 u i n o l y l , 5 O o / ~ , m . p . 2 3 6 - 2 3 7 *C 40 Quinoline Aldehydes Pentyl nitrite and 4-acetylquinoline gave with sodium ethoxide the aldehyde oxime 62;2723-acetylquinoline reacted CO CH =NOH 6 2 , m p. 267 6 4 . 2 6 1 . 27 4 63 64,87%, rn. p . p. 1 3 2 - 133 "C Quinoline Aldehydes 41 Selenium dioxide oxidation of 3-acetylquinoline in dioxane gave the ketoaldehyde 6 ' .

5-197 SC Ox 252-253 170 7 199 184 184 184 I84 184 198 198 L 198 J 4 13 2 EL Y 0 P 3 2 -. 7 Q-8-OCHIPh, HCI Natural product 8-HO-Q-4-CHO. AcZO 4-Me-S,S-diMeO-Q,SeO,, dioxane 4-Me-5,8-diMe0-6-N02-Q,SeO,, dioxane 4-Me-5,8-diMeO-6-AcNH-Q,SeO,, dioxane 4-Me-6-MeO-Q, SeO,, xylene 4-Me-6-MeO-Q, SeO, eMed-MeO-Q, SO,,130-140°C (4-Me-6-MeO-Q-2-S),, SeO,, dioxane 4-Me-6,7-diMeO-Q,SeO,, dioxane 4-Me-6-Me0-8-N02, SeO,, AcOH 4-Me-8-MeO-Q, SeO,, dioxane 4-Me-8-PhCH ,O-Q SeO,, dioxane, AcOH, AcZO 2-CI-4-CHBr,-Q, Ag NO, 4-Me-6-CI-Q, SeO,, dioxane 4-Me-6, 8-diCI-Q.

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