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Preparation of new dihydrofuro[2,3‐ f ]indole derivatives
Author(s) -
Plattner J. J.,
Parks J. A.
Publication year - 1983
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.5570200443
Subject(s) - chemistry , indole test , dehydrogenation , claisen rearrangement , substituent , acetic acid , bicyclic molecule , medicinal chemistry , ullmann reaction , organic chemistry , stereochemistry , catalysis
The preparation of new dihydrofuro[2, 3‐ f ]indole derivatives and their fully aromatic counterparts is described. Key steps in the synthesis include a Claisen rearrangement/ m ‐chloroperoxybenzoic acid oxidation sequence to form a dihydrobenzofuran intermediate and an iron/acetic acid reductive cyclization to generate the dihydrofuro[2, 3‐ f ]indole nucleus. Introduction of a 5‐phenyl substituent on the indole nitrogen was effected by a modified Ullmann reaction. Fully aromatic furo[2, 3‐ f ]indoles were obtained from the dihydro congeners by dehydrogenation with 2, 3‐dichloro‐5, 6‐dicyano‐1, 4‐benzoquinone.