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An Assessment of Electrophilic N‐Transfer of Oxaziridine with Different 2‐, 3‐, and 4‐Carbon Donor–Acceptor Substrates to Furnish Diverse N‐Containing Heterocycles in a Single Step
Author(s) -
Ghosh Asit,
Chawla Vatan,
Banerjee Prabal
Publication year - 2019
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.201900589
Subject(s) - oxaziridine , chemistry , stereocenter , electrophile , acceptor , amine gas treating , combinatorial chemistry , molecule , carbon fibers , organic chemistry , stereochemistry , enantioselective synthesis , catalysis , physics , materials science , composite number , composite material , condensed matter physics
An assessment of the scope and limitations of electrophilic N ‐transfer of oxaziridine in the presence of MgI 2 has been carried out with different donor–acceptor carbon substrates. One step access to multifunctional three‐, four‐, and five‐membered N‐containing heterocycles has been demonstrated. The different donor and acceptor substituents present in the carbon substrates play a crucial role in determining the feasibility of the N ‐transfer process. This study portrays the possibilities to incorporate amine functionality in the molecules required for the synthesis of useful drug or modification of drug for a particular response. In addition, the generation of new stereocenters in the N‐containing heterocycles through this single‐step process offers favorable scopes for the synthesis of valuable drug molecules.