Nucleophilic substitutions of 2-chloronaphtho[2,3-b]furan-4,9-dione with amines

Autor: Akira Tanaka, Katsumi Yamamoto, Kouji Nakayama, Jyunichi Koyanagi, Masayuki Ogawa
Rok vydání: 1998
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 35:301-305
ISSN: 1943-5193
0022-152X
DOI: 10.1002/jhet.5570350207
Popis: 2-Chloronaphtho[2,3-b]furan-4,9-dione 4 was allowed to react with pyrrolidine to produce 2-(1-pyrrolidinyl)naphtho[2,3-b]furan-4,9-dione 8 in 64% yield. In a similar manner, the reaction of 4 with cyclic amines (piperidine, morpholine, 4-substituted piperazines, etc.) gave the desired compounds. 2-Dimethylaminonaphtho[2,3-b]furan-4,9-dione 20 and 2-propylaminonaphtho[2,3-b]furan-4,9-dione 23 were obtained from the reactions of 4 with amines in 67% and 48% yields, respectively. Furthermore, the reactions of 4 with acyclic amines (diethylamine, dipropylamine, isopropylamine, butylamine, etc.) gave the desired compound. Compound 4 was treated with sodium azide to give 2-azidonaphtho[2,3-b]furan-4,9-dione 28 in 42% yield. All these nucleophilic substitutions were carried out at room temperature. It was found that 4 showed high reactivity for amines. Unexpectedly, 2-morpholinonaphtho[2,3-b]furan-4,9-dione 13 was obtained from the reaction of 4 with 1-morpholino-1-cyclohexene.
Databáze: OpenAIRE
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