Solid-Phase Synthesis of 3,4-Dihydroquinoxalin-2(1H)-ones via the Cyclative Cleavage of N-Arylated Carboxamides

• Authors: CARBAIN Benoit, Jean-Pierre; SCHUTZNEROVA E.; PRIBYLKA A.; KRCHNAK V.
• Year of publication: 2016
• Type: Article in Periodical
• Magazine / Source: ADVANCED SYNTHESIS & CATALYSIS
• MU Faculty or unit: Faculty of Science
• Doi: http://dx.doi.org/10.1002/adsc.201500826
• Field: Organic chemistry
• Keywords: C-N bond formation; cyclization; heterocycles; N-arylation; nitrobenzenesulfonamides; solid-phase synthesis; traceless synthesis
• Description: 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.

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