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A Lewis Acid Mediated Schmidt Reaction of Benzylic Azide: Synthesis of Sterically Crowded Aromatic Tertiary Amines
Author(s) -
Murali Annamalai,
Puppala Manohar,
Varghese Babu,
Baskaran Sundarababu
Publication year - 2011
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.201100674
Subject(s) - chemistry , schmidt reaction , steric effects , azide , lewis acids and bases , iminium , tertiary amine , alkyl , medicinal chemistry , amine gas treating , ring (chemistry) , organic chemistry , catalysis
An efficient one‐pot synthesis of sterically hindered aromatic tertiary amines through Lewis acid induced intermolecular Schmidt reaction of benzylic azides is described. In the presence of EtAlCl 2 , benzylic azide underwent a smooth Schmidt reaction to give the corresponding iminium ion, which, upon reduction with NaBH 4 in situ, afforded the tertiary amine. The effects of substituents on the aromatic ring and the steric effects of the alkyl side chain have also been studied.