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Synfacts 2010(10): 1120-1120  
DOI: 10.1055/s-0030-1258614
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Bischler-Napieralski Synthesis of Phenanthridines

Contributor(s): Victor Snieckus, Johnathan Board
J. Xi, Q.-L. Dong, G.-S. Liu, S. Wang, L. Chen*, Z.-J. Yao*
Nanjing University and Yunnan Nationalities University, Kunming, P. R. of China
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Publication History

Publication Date:
22 September 2010 (online)

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Significance

Reported is the Hendrickson reagent mediated Bischler-Napieralski synthesis of substituted phenanthridines. A mechanism following the classical proposal is given, whereby the Hendrickson reagent reacts with the amide group to form structure A, which then participates in a Friedel-Crafts reaction with the remote aromatic ring. This is consistent with the observed substituent effects, for example, R³ = 3-NO2 fails to undergo reaction. The reaction is not affected by the electronics of the amide; however, it is sensitive to steric effects.