Novel 1,4-benzodiazepines from acylnitroso-derived hetero-Diels-Alder cycloadducts.
[reaction: see text] N(4)-Hydroxy-1,4-benzodiazepines were synthesized in a single step from synthetically versatile acylnitroso-derived hetero-Diels-Alder cycloadducts. The efficiency of this transformation was found to be dependent on the NH pK(a) of the cycloadduct sulfonamide.
Surman
Matthew D
MD
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
Mulvihill
Mark J
MJ
Miller
Marvin J
MJ
D001569:Benzodiazepines / Q000138:chemical synthesis*; D003500:Cyclization; D007202:Indicators and Reagents; D009603:Nitroso Compounds / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry
D007202:Indicators and Reagents; D009603:Nitroso Compounds; D013449:Sulfonamides; D001569:Benzodiazepines