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Synthesis of spiro[cycloalkane‐1,3′‐[3 H ]indoles] from cycloalkanecarbaldehydes. Acid‐catalyzed rearrangement to cycloalkano[ b ]indoles
Author(s) -
Rodríguez J. G.,
Benito Y.,
Temprano F.
Publication year - 1985
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.5570220512
Subject(s) - cycloalkane , chemistry , catalysis , solvent , organic chemistry , solid acid , medicinal chemistry
Spiro[cycloalkane‐1,3′‐[3 H ]indoles] 2 can be obtained from the cycloalkanecarbaldehydes 1 by the Fischer reaction of their phenylhydrazones. These cyclizations are sensitive to the acid catalyst, solvent and temperature employed. Rearrangement of the 2 to the homologous cycloalkane derivatives 3 can occur by an acid catalyst or by thermal treatment of 2 in ethyleneglycol.