CONDENSATION INDOLE NAPHTHOQUINONE - SYNT HESIS OF A NEW INDOLYL-1,4-NAPHTHOQUINONE SERIES/

Addition of an indole, which does not have a group at the 3-position, to 1,4-naphthoquinone leads to the expected 2-(3-indolyl)-1,4-naphthoq uinone. When the 1,4-naphthoquinone is substituted at the 2-position b y an alkyl or aryl group, the e-substituted 3-(3-indolyl)-1,4-naphthoq uinone is easily formed. However, when the e-substituent of the quinon e is functional (OH, OMe, Cl, Br, NC5H10, S-C6H5), in addition to the new series of expected indolylnaphthoquinones, several by-products res ulting from elimination of the 2-substituted and/or further reaction o f these compounds are formed. The outcome at the reaction appears to b e very sensitive to the experimental conditions.