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).
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Shiotani et al. (1982) studied this question.
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