Chemical Transformation of Protoberberines. VII. Efficient Conversion of Protoberberines into Benzindenoazepines via 8, 14-Cycloberbines
A simple and convenient transformation of berberine (1) into trans-, cis-, and unsaturated benzindenoazepines through regioselective C14-N bond cleavage of 8, 14-cycloberbines is described. Acidic treatment of the 8, 14-cycloberbine (2) effected regioselective ring opening to afford the trans-and ci...
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Veröffentlicht in: | Chemical & pharmaceutical bulletin 1985/04/25, Vol.33(4), pp.1434-1443 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A simple and convenient transformation of berberine (1) into trans-, cis-, and unsaturated benzindenoazepines through regioselective C14-N bond cleavage of 8, 14-cycloberbines is described. Acidic treatment of the 8, 14-cycloberbine (2) effected regioselective ring opening to afford the trans-and cis-benzindenoazepines (7a and 7b) as the kinetically and thermodynamically controlled products, respectively. Dehydration of their N-methyl derivatives (11a and 11b) gave the unsaturated benzindenoazepine (20), which was obtained more efficiently from the 8, 14-cycloberbine (2) by treatment with p-toluenesulfonic acid in benzene followed by N-methylation. Similarly, the ring D-inverted 8, 14-cycloberbine (23) was converted to the corresponding trans-, cis-, and unsaturated benzindenoazepines (24a, 24b, and 27, respectively). |
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ISSN: | 0009-2363 1347-5223 |
DOI: | 10.1248/cpb.33.1434 |