Chemija / Chemistry
 ISSN 0235-7216 ISSN 2424-4538 (online) |
2012 m. Nr. 4 Synthesis and microwave-promoted Suzuki-Miyaura cross- zoupling reactions of 5-bromo-1,3,3-trimethyl-1,3- dihydro-6ʹH-spiro[indole-2,2ʹ-piperidin]-6ʹ-one
The aza-Michael addition reaction of 5-bromo-1,3,3-trimethyl-2-methylidene-2,3-dihydro-1H-indole with acrylamide and the following cyclization afforded 5-bromo-1,3,3-trimethyl-1,3-dihydro-6'H-spiro[indole-2,2'-piperidin]-6'-one. The microwave-promoted Suzuki-Miyaura coupling of the latter compound with arylboronic acids gave the 5-arylated products with good to excellent yields. The reductive ring-opening reaction of 5-(naphthalen-2-yl)spiro[indole-2,2'-piperidin]-6'-one and following chemical transformations yielded the corresponding indoline derivatives possessing 2-[3-(ethoxycarbonyl) propyl]- and 2-(4-aminobutyl)-side chains.
Keywords: indole, spiro[indole[2,2']piperidine], Suzuki-Miyaura cross-coupling, microwave, cesium carbonate, fluorescence |
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