J 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. KRCHNAK

Basic 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

Tags

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
Name: Zaměstnáním nejlepších mladých vědců k rozvoji mezinárodní spolupráce