A Lewis Acid Mediated Schmidt Reaction of Benzylic Azide: Synthesis of Sterically Crowded Aromatic Tertiary Amines | Zendy

Murali Annamalai | Zendy; Puppala Manohar | Zendy; Varghese Babu | Zendy; Baskaran Sundarababu | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research