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Synthesis of phenyl furyl sulfides and phenyl furyl ethers by nucleophilic substitution of nitrofurans

✍ Scribed by Masayuki Ogawa; Katsuya Sakuma; Hiroshi Okamoto; Jyunichi Koyanagi; Kouji Nakayama; Akira Tanaka; Katsumi Yamamoto

Publisher: Journal of Heterocyclic Chemistry
Year: 2007
Tongue: English
Weight: 213 KB
Volume: 44
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570440527

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✦ Synopsis

Abstract

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Phenyl furyl sulfides (3a‐j) and phenyl furyl ethers (3k‐n), which are useful in synthesizing furocondensed 3‐ring compounds, can be synthesized by nucleophilic substitution of nitrofurans having electron withdrawal groups. In our experiments using 5‐nitrofurans having electron withdrawal groups (2a‐i), nucleophilic substitution readily occurred with the benzenethiolate anion of thiosalicylic acid (1a), the benzenethiolate anion of thiosalicylate ester (1b), and the phenylate anions of salicylate esters (1c‐d) to yield phenyl furyl sulfides (3a‐j) and phenyl furyl ethers (3k‐n).

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