2006
DOI: 10.1002/chin.200636146
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Isonitrile Trapping Reactions under Thermolysis of Alkoxyamines for the Synthesis of Quinolines.

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“…The reaction was highly amenable to alkyl 22 e , cyclopropyl 22 f , electron‐rich (4−CH 3 , 4−OCH 3 ) as well as electron‐poor (4−CF 3 , 4−NO 2 ) arylsulfonamides, anilines, benzamide, morpholine and piperidine as electron‐rich exogenous external amine source. Slight catalyst poisoning and amino‐chlorination [105] (side product) formation was observed in case of piperidine, which was greatly minimised by addition of diethylsalicylamide [106–107] (40 mol %). Low temperature (<85 °C) and molecular sieves presence was critical to drive this intra/inter‐molecular diamination efficiently and broadly because Cbz or sulphonyl protected hydroxylamine substrates were decomposed at higher temperature.…”
Section: Introductionmentioning
confidence: 99%
“…The reaction was highly amenable to alkyl 22 e , cyclopropyl 22 f , electron‐rich (4−CH 3 , 4−OCH 3 ) as well as electron‐poor (4−CF 3 , 4−NO 2 ) arylsulfonamides, anilines, benzamide, morpholine and piperidine as electron‐rich exogenous external amine source. Slight catalyst poisoning and amino‐chlorination [105] (side product) formation was observed in case of piperidine, which was greatly minimised by addition of diethylsalicylamide [106–107] (40 mol %). Low temperature (<85 °C) and molecular sieves presence was critical to drive this intra/inter‐molecular diamination efficiently and broadly because Cbz or sulphonyl protected hydroxylamine substrates were decomposed at higher temperature.…”
Section: Introductionmentioning
confidence: 99%