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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 and 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, vol.~358, No~5, p.~701-706. ISSN~1615-4150. Available from: https://dx.doi.org/10.1002/adsc.201500826.
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