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Alkylation of cycloalkano[ B ]indoles via indolylmagnesium salts: Synthesis of 3 h ‐indoles and oxidative rearrangement to spiro[cycloalkane‐1,2′‐indolin]‐3′‐ones
Author(s) -
Rodriguez JosÈGonzalo,
Andrès Angel San
Publication year - 1991
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.5570280522
Subject(s) - chemistry , cycloalkane , alkylation , methyl iodide , halide , alkyl , medicinal chemistry , selectivity , derivative (finance) , iodide , organic chemistry , catalysis , financial economics , economics
Alkylation of cycloalkano[ b ]indolylmagnesium iodide with alkyl halides has been analyzed to prepare cycloalkano‐3 H ‐indoles, methyl and N,N ‐dimethylpropyl derivatives. Spiro[cycloalkane‐1,2′‐indolin‐3′‐one] derivatives appear as secondary products in this reaction. Selectivity and optimization of the reaction has been determined and a mechanism for the formation of the spiro derivative is proposed.