Quinolines Friedlander synthesis

Free Electron Molecular Orbital method colour and constitution, 1, 342 Freelingyne occurrence, 4, 706 Free radical processes in photography, 1, 387-389 Friedlander synthesis quinolines, 2, 443 thioindigo dyes, 4, 910 Fries rearrangement chroman-4-one synthesis from, 3, 850 Fructose, 1-deoxy- C NMR, 4, 575 Frusemide as diuretic, 1, 174 metabolism, 1, 245 FS-32 — see 1/f-Indazole, l-[3-... 

Friedlander synthesis, 2, 445 Quinoline, alkenyl-1,2-dihydro-disproportionation, 2, 369 Quinoline, 2-alkoxy-reactions, 2, 351 Quinoline, 4-alkoxy-reactions, 2, 351 Quinoline, 2-alkoxy-4-hydroxy-synthesis... 

Friedlander synthesis, 2, 444 Quinoline, 2-aryl-4-phenyl-synthesis... 

Friedlander synthesis, 2, 443 Quinoline, perhydro-conformation, 2, 160 synthesis, 2, 376 Quinoline, 2-phenyl-reactions... 

Friedlander synthesis, 2, 444 as antipyretic, 1, 172 Quinoline-4-carboxylic acids amination, 2, 236 Beyer synthesis, 2, 475 Pfitzinger synthesis, 2, 446... 

Friedlander synthesis org chem A synthesis of quinolines the method is usually catalyzed by bases and consists of condensation of an aromatic p-amino-carbonyl derivative with a compound containing a methylene group in the alpha position to the carbonyl. fred.lan dar. sin-tha-sas ... 

The most important synthesis in this class is that of quinolines, due to Friedlander, with its major modifications by Pfitzinger and by von Niementowski. The Friedlander synthesis has been comprehensively reviewed (77HC(32-1)181, 820R(28)37, 80T2359), the last two reviews dealing only with the true Friedlander procedure. This is exemplified in equation (52), and the various possible modifications are indicated by the substituents. 

A reaction which formally resembles a Friedlander synthesis is that between o-aminobenz-aldehyde and iodobenzene, the resulting 2-formyldiphenylamine being cyclized by acid to give acridine (17CB1306). Quinolines (372) can be synthesized by passing mixtures of o-nitrobenzaldehyde and alcohols over a Cu-Ni-V205 catalyst at 300-320 °C (76MI20801). 

The Friedlander synthesis of quinolines has been adapted to give derivatives of compounds (279) and (280). The isomeric quinoline aldehydes (284) and (285) react with various ketones to give (286) and (287) (77CR(C)(284)459, 82JHC1289). Compound (286) has also been obtained starting from the Schiff s base derivative of (284) (81JHC925). 

Quinoline, 5-nitro-oxidation, 2, 210 synthesis, 2, 318 Quinoline, 6-nitro-nitration, 2, 318 Quinoline, 7-nitro-nitration, 2, 318 synthesis, 2, 318 Quinoline, 8-nitro-Doebner-von Miller synthesis, 2, 466 synthesis, 2, 318 Quinoline, 3-pentyl-Friedlander synthesis, 2, 443 Quinoline, perhydro-conformation, 2, 160 synthesis, 2, 376 Quinoline, 2-phenyl-reactions... 

Using an environmentally benign Friedlander synthesis, Yang and co-workers synthesized 11 //-indeno[ l, 2,/)Jquinolincs in refluxing ethanol and a catalytic amount of sodium ethoxide <07T7654>. This method provided a very nice complement to quinoline synthesis through the Friedlander reaction while avoiding harsh reaction conditions. 

In the simplest of these, jS-enaminones are synthesized (equation 129) by the addition of amines to 1,3-diketones or /3-ketoesters. The reaction has been apphed to the Friedlander synthesis of quinolines by condensation of the enaminone and other carbonyl present in the substrate. Substituted pyrroles in equation (130) can be obtained as well when a propargyl group is present, by addition of the enaminone to the triple bond. Alcohols, thiols, and secondary phosphines have been also tested as nucleophiles with good results. A particularly interesting case is found in the condensation of indoles with 1,3-diketones to give substituted indol derivatives in equation (131). ... 

---