Synthesis of indolylquinolines under Friedel-Crafts reaction conditions

Article abstract of DOI:10.1016/S0040-4020(01)89272-3

A one-pot synthesis of some novel indolylquinoline analogues of biological interest using indole or its 5-substituted derivatives as substrates under Friedel-Crafts acylation conditions is reported. The synthesis of the compounds was accomplished by the employment of excess amounts of the substrates and higher temperature. The complete structure of the derivative obtained by using indole as substrate and dichloroacetyl chloride as acylating agent was unequivocally established as 2-(2''-dichloroacetamidobenzyl)-3-(3'-indolyl)-quinoline 2a by single crystal X-ray analysis. The structures of other similar indolylquinolines 2b-2e and 3 were defined by spectroscopic analysis. The mechanism of formation of the analogues has also been rationalised.