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Efficient photochemical synthesis of tricyclic keto‐indoles
Author(s) -
Tietcheu Christèle,
Garcia Christophe,
Gardette Daniel,
Dugat Denise,
Gramain JeanClaude
Publication year - 2002
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.5570390517
Subject(s) - chemistry , tricyclic , benzene , methanol , photodissociation , ring (chemistry) , base (topology) , photochemistry , sodium , combinatorial chemistry , organic chemistry , mathematical analysis , mathematics
Tricyclic keto‐indoles were synthesized by photocyclization of easily obtained enaminones in an electro‐cyclic photochemical reaction. The three methods reported were chosen according to the enaminone structure. The most general procedure using one‐step synthesis was carried out in a benzene‐methanol solution in the presence of sodium methylate. In the case of base sensitive substrates, the best method was photocyclization followed by oxidation. Besides, N ‐unsubstituted indoles with a five‐membered ring were prepared by a photolysis reaction. All three methods are efficient and easy to perform.