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Communication | Regular issue | Vol 19, No. 3, 1982, pp.515-520
Published online, 1st January, 1970
DOI: 10.3987/R-1982-03-0515
Meldrum’s Acid in Organic Synthesis 3. Synthesis of 2-Substituted Indoles from Phenylhydroxylamine

Kunihiko Mohri, Yuji Oikawa, Ken-ichi Hirao, and Osamu Yonemitsu

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan


Treatment of phenylhydroxylamine oxalate with acyl Meldrum’s acids in boiling acetonitrile readily gave N-acylacetylphenylhydroxylamines, which were converted to 2-substituted indoles by another treatment with acyl Meldrum’s acids in refluxing toluene. N-Benzoyl, N-acetyl, and N-benzyloxycarbonyl derivatives of phenylhydroxylamine were treated with phenylacetyl Meldrum’s acid in boiling benzene, followed by treatment with hydrochloric acid in ethanol to give the corresponding N-acyl-2-benzylindoles.