Quinolines Smiles rearrangement

Skraup quinoline synthesis, 443 Smiles rearrangement, phenothiazine, 534 Spiroalkylation, 222, 280 Spirocyclization, conjugate addition, 386 Spiroimidazolone formation, 335 Spiropyrazolopiperidine, 375 Stannylation, alkyne, 15 Stereoselective dehydration, 198 Grignard addition, 198, 199 reduction, 129, 226 hydroxyketone, 400 iminoketone beta, 553 oxazaborohydride, 585 transfer chirality, 321 Stilbene formation, self alkylation, 525 Stobbe condensation, benzophenone, 103... 

Weidner ef alP described a one-pot Smiles rearrangement method for the synthesis of various aminoquinolines from the corresponding hydroxyquinolines and showed that the tendency for the conversion depends on the electron-deficient nature of the quinolines. In a specific example, the reaction of 15 with (i) 2-bromo-2-methylpropionamide, 3 equiv. each of NaH and cesium carbonate in dioxane at reflux for 16 h and (ii) N-methylpyrrolidinone (NMP), l,3-dimethyl-3,4,5,6-tetrahydro-2(l//)-pyrimidinone (DMPU) (10 1 ratio) and 1 equiv. of NaH at 150 C for 72 h afforded the amine 16. 

Sandmeyer synthesis (isatin) 145 Schmidt-Druey synthesis (pyridazine) 461 Schollkopf synthesis (oxazole) 173 Sharpless-Katsuki epoxidation 24 Shaw synthesis (pyrimidine) 468 Skraup-Doebner-Miller synthesis (quinoline) 400 Smiles rearrangement 446 Sommelet-Hauser rearrangement 136 Staudinger reaction 53 Steglich reagent (DMAP) 348 Stork isoxazole annelation 191... 

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