Synthesis and reactivity of new dihydroisoquinoline-derived oxaziridines

Abstract

N-Alkyl oxaziridines react as oxygenating reagents in the presence of a nucleophile. In this work, we describe the synthesis of new dihydroisoquinoline oxaziridines, and their reactivity in an acid-promoted reaction both in presence and in absence of sulfides. In the absence of sulfides, a new nitrone is produced.

Recent Advances in the Preparations and Synthetic Applications of Oxaziridines and Diaziridines

“…The authors extended their study via incorporation of −NO 2 group in the aromatic ring of 22 to synthesize 25 via 24 . The synthesized compounds ( 25 ) were employed to oxidize sulfides [26,27] . It was revealed that due to the presence of trichloromethyl ( 23 ) and nitro groups ( 25 ) on the dihydroisoquinoline skeleton, the oxaziridine became more electrophilic and the reaction of oxygen transfer into sulphide occured in absence of acid (see section 3.1.2).…”

“…Consequently, it was reported that the presence of p ‐chlorophenyl group and two nitro groups on the dihydroisoquinoline skeleton ( 91 c and 91 d ) made oxaziridine more electrophilic and led to good sulfoxide conversion from sulfide 88 in short time (15 min and 5 min). Interestingly, the unsubstituted oxaziridines ( 91 a and 91 b ) yielded corresponding nitrones 93 quantitatively (Scheme 23b) [27] . The different substituents at positions 1 and 7 on the dihydroisoquinoline skeleton were primarily responsible for the formation of sulfoxides/nitrones via the oxidation of oxaziridines.…”

“…Interestingly, the unsubstituted oxaziridines (91 a and 91 b) yielded corresponding nitrones 93 quantitatively (Scheme 23b). [27] The different substituents at positions 1 and 7 on the dihydroisoquinoline skeleton were primarily responsible for the formation of sulfoxides/nitrones via the oxidation of oxaziridines.…”