title: Palladium-catalyzed regiocontrolled domino synthesis of N-sulfonyl dihydrophenanthridines and dihydrodibenzo[c,e]azepines: control over the formation of biaryl sultams in the intramolecular direct arylation.
abstract: A palladium-catalyzed domino N-benzylation/intramolecular direct arylation involving sulfonanilides and 2-bromobenzyl bromides has been developed for the first time, providing a workable access to N-sulfonyl dihydrophenanthridines in good to excellent yields. Under the optimized conditions, the formation of 5,6-dihydrophenanthridines was largely controlled over the formation of biaryl sultams containing a seven member ring. The optimized condition was found extendable to the regiocontrolled domino formation of N-sulfonyl-6,7-dihydro-5H-dibenzo[c,e]azepines over the biaryl sultam formation. Using an appropriate substrate, a biaryl sultam has been obtained exclusively.
authors.affiliation: Department of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research , S. A. S. Nagar, Punjab 160062, India.
authors.forename: Joydev K
authors.initials: JK
authors.lastname: Laha
authors.forename: Neetu
authors.initials: N
authors.lastname: Dayal
authors.forename: Roli
authors.initials: R
authors.lastname: Jain
authors.forename: Ketul
authors.initials: K
authors.lastname: Patel
mesh_terms: D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry*
chemical_list: D001381:Azepines; D010617:Phenanthridines; D013450:Sulfones; D010165:Palladium