SYNTHESIS OF BIHETEROCYCLES CONTAINING INDOLE NUCLEUS

Abstract

Indole-2-carboxyhydrazides (2) when reacted with phenacylbromide or chloroacetone in dry ethanol and DMF yield 2-(6'-phenyl/methyl-1',2',4'-triazin-3'-yl)indoles (5 and 7). A suitable reaction mechanism for the formation of these compounds (5 and7) has been proposed. 2-(1',2',5',6'-Tetrahy-dro-5'-oxo-1',2',4'-triazin-3'-yl)indoles (8) have been prepared from the corresponding hydrazides (2) by the reaction with chloroacetamide in dry DMF. 1-Aryl-3-(indol-2'-yl)ureas (10), obtained from the carboxyazides (9), afford 3-aryl-1-(indol-2'-yl)-2,3-dihydro-2-oxo-pyrimidine-4,6(1H,5H)diones (11) when refluxed with diethyl malonate and sodium ethoxide in dry ethanol. The mass spectral fragmentations of these new series of compounds have been discussed.