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@article{1380294, author = {Carbain, Benoit, JeanandPierre and Schutznerova, E. and Pribylka, A. and Krchnak, V.}, article_location = {WEINHEIM}, article_number = {5}, doi = {http://dx.doi.org/10.1002/adsc.201500826}, keywords = {C-N bond formation; cyclization; heterocycles; N-arylation; nitrobenzenesulfonamides; solid-phase synthesis; traceless synthesis}, language = {eng}, issn = {1615-4150}, journal = {ADVANCED SYNTHESIS & CATALYSIS}, title = {Solid-Phase Synthesis of 3,4-Dihydroquinoxalin-2(1H)-ones via the Cyclative Cleavage of N-Arylated Carboxamides}, volume = {358}, year = {2016} }
TY - JOUR ID - 1380294 AU - Carbain, Benoit, Jean-Pierre - Schutznerova, E. - Pribylka, A. - Krchnak, V. PY - 2016 TI - Solid-Phase Synthesis of 3,4-Dihydroquinoxalin-2(1H)-ones via the Cyclative Cleavage of N-Arylated Carboxamides JF - ADVANCED SYNTHESIS & CATALYSIS VL - 358 IS - 5 SP - 701-706 EP - 701-706 PB - WILEY-V C H VERLAG GMBH SN - 16154150 KW - C-N bond formation KW - cyclization KW - heterocycles KW - N-arylation KW - nitrobenzenesulfonamides KW - solid-phase synthesis KW - traceless synthesis N2 - We describe a practical (time-efficient, with commercially available building blocks, user friendly reaction conditions, high purity of products) synthesis of pharmacologically relevant quinoxalinones with three points of diversification that takes advantage of solid-phase synthesis and cyclative cleavage. Resin-bound (S)-2-(N-alkyl-2-nitrophenyl) sulfonamide-3-alkyl-N-(2-hydroxyethyl) propanamides, which are accessible from Fmoc-protected a-amino acids, 2-nitrobenzenesulfonyl chloride and alcohols, underwent base-mediated N-arylation. The reduction of the nitro group produced acyclic intermediates that were subjected to acid-mediated cyclative cleavage to yield 3,4-dihydroquinoxalin-2(1H)-ones. ER -
CARBAIN, Benoit, Jean-Pierre, E. SCHUTZNEROVA, A. PRIBYLKA a V. KRCHNAK. Solid-Phase Synthesis of 3,4-Dihydroquinoxalin-2(1H)-ones via the Cyclative Cleavage of N-Arylated Carboxamides. \textit{ADVANCED SYNTHESIS \&{}amp; CATALYSIS}. WEINHEIM: WILEY-V C H VERLAG GMBH, 2016, roč.~358, č.~5, s.~701-706. ISSN~1615-4150. Dostupné z: https://dx.doi.org/10.1002/adsc.201500826.
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