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Six 10-hydroxy-4-methyl-2,3,4,5,6,7-hexahydro-1,6-methano-1H-4-benzazonine derivatives 17a-f have been synthesized as potential analgesics. The synthesis of these compounds involved conversion of 4-(2-dimethylaminoethyl)-6-methoxy alpha tetralone derivatives 12a-f to their N-methyl analogues and the subsequent intramolecular mannich reaction with formaldehyde to give the 7-keto C-ring homobenzomorphans 14a-f from which 17a-f, respectively, were obtained. Compounds 17a-f are as potent as morphine as analgesics (mice).

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The parent framework of furo[2,3‐c]pyridine has been synthesized. 3‐Furoic acid chloride (2) was reduced with bis(triphenylphosphine) copper(1) tetrahydroborate to afford 3‐furaldehyde (3) which was condensed with malonic acid to give β‐(3‐furyl)acrylic acid (4). The acrylic acid 4 was converted to the acid azide (5), which in turn was cyclized to give furo[2,3‐c]pyridin‐7(6H)‐one (6) by heating at 180° in diphenylmethane. The pyridone 6 was chlorinated with phosphorus oxychloride, followed by reduction with zinc and acetic acid to give furo[2,3‐c]pyridine (8).