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Solid‐Phase Synthesis of 3,4‐Dihydroquinoxalin‐2(1 H )‐ones via the Cyclative Cleavage of N ‐Arylated Carboxamides
Author(s) -
Carbain Benoit,
Schütznerová Eva,
Přibylka Adam,
Krchňák Viktor
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500826
Subject(s) - chemistry , alkyl , cleavage (geology) , yield (engineering) , solid phase synthesis , nitro , chloride , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , peptide , biochemistry , materials science , geotechnical engineering , fracture (geology) , engineering , metallurgy
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 α‐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(1 H )‐ones.