Furopyridines. I. Synthesis of furo[2,3‐ c ]pyridine | Zendy

Shiotani Shunsaku | Zendy; Morita Hiroyuki | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

Furopyridines. I. Synthesis of furo[2,3‐ c ]pyridine

Author(s) -

Shiotani Shunsaku,

Morita Hiroyuki

Publication year - 1982

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570190544

Subject(s) - chemistry , pyridine , triphenylphosphine , acetic acid , malonic acid , acrylic acid , zinc , chloride , medicinal chemistry , azide , organic chemistry , catalysis , copolymer , polymer

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(6 H )‐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 ).

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research