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Carbene‐Catalyzed Aroylation of a 2‐Chloroquinoxaline N ‐Oxide with Aromatic Aldehydes at Room Temperature
Author(s) -
Maichrowski Jan,
Bhasin Aman,
Sasse Florenz,
Kaufmann Dieter E.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402252
Subject(s) - chemistry , carbene , catalysis , nitrone , iodide , oxide , medicinal chemistry , organic chemistry , combinatorial chemistry , cycloaddition
Starting from easily accessible 2‐chloro‐3‐(cyclopentyloxy)‐7‐fluoroquinoxaline 1‐oxide, 12 new biologically promising aroylquinoxaline N ‐oxides were synthesized through carbene‐catalyzed aroylation of the chloro nitrone unit with different aromatic aldehydes in the presence of 1,3‐dimethylimidazolium iodide as the carbene precursor. The optimized reaction conditions tolerated a broad bandwidth of aldehydes and allowed the synthesis of the corresponding ketones in yields up to 87 %. Studies of their biological activities resulted in interesting specific cytotoxic effects against tumor cell lines.