Yb(OTf)3-Catalyzed Bromination Reactions of Natural Product-like N-Benzyl Cinnamamides: A Facile Route to Diverse N-Substituted Amides of Pharmacological Interest

Author(s): Carlos E. Puerto Galvis, Jose G. Hernandez Barajas, Vladimir V. Kouznetsov.

Journal Name: Current Organic Chemistry

Volume 17 , Issue 14 , 2013

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Abstract:

Diverse natural product-like N-benzyl cinnamamides were prepared by condensation of trans-cinnamic acid with substituted benzylamines in the presence of boric acid as catalyst. The further evaluation of this amides as a substrates of the bromo-arylation reaction, in the presence of N-bromosuccinimide (NBS) as the halogen source and under the catalysis of Yb(OTf)3, generate a different types of N-substituted amides: N-aryl 2,3-dibromopropanamides, N-(2-bromobenzyl) cinnamamides and tetrahydro-2-benzazepin-3-one as a new molecules. Here we discuss the formation of these main products on the basis of the electronic nature of the substituents present in the N-benzyl aromatic ring of the prepared cinnamamides.

Keywords: N-Aryl 2, 3-dibromopropanamides, N-Benzyl cinnamamides, Boric acid, N-(2-Bromobenzyl) cinnamamides, Tetrahydro-2- benzazepin-3-ones, Yb(OTf)3-Catalyzed bromination reactions.

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Article Details

VOLUME: 17
ISSUE: 14
Year: 2013
Page: [1545 - 1554]
Pages: 10
DOI: 10.2174/1385272811317140009
Price: $58

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