Synthesis of quinazolines from N-(2-nitrophenylsulfonyl)iminodiacetate and alpha-(2-nitrophenylsulfonyl)amino ketones via 2H-indazole 1-oxides.
Base-catalyzed rearrangement of 2H-indazoles 1-oxides, prepared by tandem carbon-carbon followed by nitrogen-nitrogen bond formations from easily accessible N-alkyl-2-nitro-N-(2-oxo-2-aryl-ethyl)-benzenesulfonamides using glycine, 2-nitrobenzenesulfonyl chlorides, and bromo ketones/acetates, yielded high purity quinazolines.
Krupková
Sona
S
Department of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Slough
Greg A
GA
Krchnák
Viktor
V
D002384:Catalysis; D007098:Imino Acids / Q000737:chemistry*; D007191:Indazoles / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009596:Nitrophenols / Q000737:chemistry*; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D013449:Sulfonamides / Q000737:chemistry*; D000096926:Benzenesulfonamides
D007098:Imino Acids; D007191:Indazoles; D007659:Ketones; D009596:Nitrophenols; D010087:Oxides; D011799:Quinazolines; D013449:Sulfonamides; D000096926:Benzenesulfonamides; C553198:N-(2-nitrophenylsulfonyl)iminodiacetate