Murali, Annamalai ; Puppala, Manohar ; Varghese, Babu ; Baskaran, Sundarababu (2011) A lewis acid mediated schmidt reaction of benzylic azide: synthesis of sterically crowded aromatic tertiary amines European Journal of Organic Chemistry, 2011 (27). pp. 5297-5302. ISSN 1434-193X
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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...
Related URL: http://dx.doi.org/10.1002/ejoc.201100674
Abstract
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 EtAlCl2, benzylic azide underwent a smooth Schmidt reaction to give the corresponding iminium ion, which, upon reduction with NaBH4 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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley and Sons. |
| Keywords: | Amines; Azides; Cyclization; Fused-ring Systems; Lewis Acids |
| ID Code: | 98538 |
| Deposited On: | 17 Sep 2014 11:22 |
| Last Modified: | 17 Sep 2014 11:22 |
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