ChemInform Abstract: Synthesis of 3,4-Bridged Indoles by Photocyclization Reactions. Part 1. Photocyclization of Halogenoacetyl Tryptophan Derivatives.
Abstract
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ChemInform Abstract
Irradiation of the chloro amide (I) followed by methylation leads to the fused indoles (III) and (IV), while photolysis of the dichloride ( V) and subsequent treatment with the nucleophiles (VI) yields 3,4- bridged indoles exclusively. In the case of the reaction in MeCN/H2O solution, the alcohol (VIIa) and the lactone (VIII) which results from spontaneous cyclization of the cis isomer of (VIIa) are obtained. Irradiation of the trichlorides (IX) in MeCN/H2O also gives the desired 3,4-bridged indoles, while the analogue (XI) is transformed into the cyclic ether (XII). Starting from the chloro amides (XIII) the fused indoles (XIV) and/or the elimination products (XV) are formed.
