Highly Regioselective Nitration Reactions Provide a Versatile Method of Functionalizing Benzocycloheptapyridine Tricyclic Ring Systems:  Application toward Preparation of Nanomolar Inhibitors of Farnesyl Protein Transferase

A comprehensive study of nitration reaction of azatricyclic systems has been carried out. Whereas classical nitrations using KNO3−H2SO4 at low temperatures gave nitrated products mainly at the 9-position, use of tetrabutylammonium nitrate−trifluoroacetic anhydride (TBAN−TFAA) resulted in exclusive n...

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Published in:Journal of organic chemistry 1998-02, Vol.63 (3), p.445-451
Main Authors: Njoroge, F. George, Vibulbhan, Bancha, Pinto, Patrick, Chan, Tze-Ming, Osterman, Rebecca, Remiszewski, Stacy, Del Rosario, Jocelyn, Doll, Ronald, Girijavallabhan, V, Ganguly, Ashit K
Format: Article
Language:English
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Summary:A comprehensive study of nitration reaction of azatricyclic systems has been carried out. Whereas classical nitrations using KNO3−H2SO4 at low temperatures gave nitrated products mainly at the 9-position, use of tetrabutylammonium nitrate−trifluoroacetic anhydride (TBAN−TFAA) resulted in exclusive nitration of the 3-position in the case carbamates 1, and 4−6 and the tricyclic ketone 7. These 3-nitro tricyclic derivatives have been valuable intermediates for the preparation of the very potent farnesyl protein transferase inhibitors such as the tricyclic pyridyl acetamide 32 and other new analogues.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo971100z