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

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F16%3A00094234" target="_blank" >RIV/00216224:14310/16:00094234 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1002/adsc.201500826" target="_blank" >http://dx.doi.org/10.1002/adsc.201500826</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/adsc.201500826" target="_blank" >10.1002/adsc.201500826</a>

Result language

angličtina

Original language name

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

Original language 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.

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/EE2.3.30.0037" target="_blank" >EE2.3.30.0037: Employment of Best Young Scientists for International Cooperation Empowerment</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2016

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

ADVANCED SYNTHESIS &amp; CATALYSIS

ISSN

1615-4150

e-ISSN

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Volume of the periodical

358

Issue of the periodical within the volume

5

Country of publishing house

DE - GERMANY

Number of pages

6

Pages from-to

701-706

UT code for WoS article

000372132100002

EID of the result in the Scopus database

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