Detailed Information on Publication Record
2016
Solid-Phase Synthesis of 3,4-Dihydroquinoxalin-2(1H)-ones via the Cyclative Cleavage of N-Arylated Carboxamides
CARBAIN, Benoit, Jean-Pierre, E. SCHUTZNEROVA, A. PRIBYLKA and V. KRCHNAKBasic information
Original name
Solid-Phase Synthesis of 3,4-Dihydroquinoxalin-2(1H)-ones via the Cyclative Cleavage of N-Arylated Carboxamides
Authors
CARBAIN, Benoit, Jean-Pierre (250 France, belonging to the institution), E. SCHUTZNEROVA (203 Czech Republic), A. PRIBYLKA (203 Czech Republic) and V. KRCHNAK (203 Czech Republic)
Edition
ADVANCED SYNTHESIS & CATALYSIS, WEINHEIM, WILEY-V C H VERLAG GMBH, 2016, 1615-4150
Other information
Language
English
Type of outcome
Článek v odborném periodiku
Field of Study
10401 Organic chemistry
Country of publisher
Germany
Confidentiality degree
není předmětem státního či obchodního tajemství
Impact factor
Impact factor: 5.646
RIV identification code
RIV/00216224:14310/16:00094234
Organization unit
Faculty of Science
UT WoS
000372132100002
Keywords in English
C-N bond formation; cyclization; heterocycles; N-arylation; nitrobenzenesulfonamides; solid-phase synthesis; traceless synthesis
Změněno: 11/5/2017 18:21, Ing. Andrea Mikešková
Abstract
V originále
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.
Links
EE2.3.30.0037, research and development project |
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