Studies on Tertiary Amine Oxides. LXXI. Some Electrophilic Reactions of 1-Hydroxy-2-phenylindole

Treatment of 1-hydroxy-2-phenylindole (1) with phosphoryl chloride-DMF gave 2-phenylindole-3-carboxaldehyde (2) in 70% yield. The reaction of 1 with quinoline 1-oxide (3) and benzoyl chloride in boiling chloroform produced 1-benzoyloxy-2-phenyl-3-(2-quinolyl) indole (5) and 1-hydroxy-2-phenyl-3-(2-q...

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Published inChemical & pharmaceutical bulletin Vol. 29; no. 7; pp. 1827 - 1831
Main Authors NAGAYOSHI, TSUYOSHI, SAEKI, SEITARO, HAMANA, MASATOMO
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1981
Japan Science and Technology Agency
Subjects
1-benzoyloxy-2-phenyl-3-(2-quinolyl) indole
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Summary:Treatment of 1-hydroxy-2-phenylindole (1) with phosphoryl chloride-DMF gave 2-phenylindole-3-carboxaldehyde (2) in 70% yield. The reaction of 1 with quinoline 1-oxide (3) and benzoyl chloride in boiling chloroform produced 1-benzoyloxy-2-phenyl-3-(2-quinolyl) indole (5) and 1-hydroxy-2-phenyl-3-(2-quinolyl) indole (6). In the reaction using tosyl chloride instead of benzoyl chloride, 6 or 2-phenyl-3-(2-quinolyl) indole (8) was formed. These results demonstrate that the enehydroxylamine systems in 1 and 1-benzoyloxy-2-phenylindole (4) can behave as nucleophilic species as a result of enamine-like polarization.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.29.1827