A one-pot synthesis of some novel indolylquinoline analogues of biolog
ical interest using indole or its 5-substituted derivatives as substra
tes under Friedel-Crafts acylation conditions is reported. The synthes
is of the compounds was accomplished by the employment of excess amoun
ts of the substrates and higher temperature. The complete structure of
the derivative obtained by using indole as substrate and dichloroacet
yl chloride as acylating agent was unequivocally established as -dichl
oroacetamidobenzyl)-3-(3'-indolyl)-quinoline 2a by single crystal X-ra
y analysis. The structures of other similar indolylquinolines 2b-2e an
d 3 were defined by spectroscopic analysis. The mechanism of formation
of the analogues has also been rationalised.