Premium
Synthesis of phenyl furyl sulfides and phenyl furyl ethers by nucleophilic substitution of nitrofurans
Author(s) -
Ogawa Masayuki,
Sakuma Katsuya,
Okamoto Hiroshi,
Koyanagi Jyunichi,
Nakayama Kouji,
Tanaka Akira,
Yamamoto Katsumi
Publication year - 2007
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.5570440527
Subject(s) - chemistry , nitrofuran , nucleophilic substitution , yield (engineering) , nucleophile , medicinal chemistry , ring (chemistry) , nucleophilic addition , organic chemistry , catalysis , genetics , materials science , metallurgy , biology
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 ).