Abstract
AbstractThe reactions of ethyl (1,4‐dihydro‐4‐oxoquinazolin‐2‐yl)acetate 4 and 2‐aminoquinazolin‐4(1H)‐one 5 with diethyl ethoxymethylenemalonate (EMME), (ethoxymethylene)malononitrile (EMMN) and ethyl (ethoxymethylene)cyanoacetate (EMCA) are reported, and rather different results are obtained to those previously found with quinoline analogs. Reaction of 4 with EMME gives a pyrido[1,2‐a]quinazoline, while with EMMN and EMCA ethyl 2‐(pyridin‐2‐yl)aminobenzoates are formed, presumably by ring‐opening of intermediate pyrido[2,1‐b]quinazolines. Reaction of 5 with EMME likewise results in ultimate cyclization onto N‐1 of the quinazoline, while the EMMN and EMCA reactions give isolable pyrimido[2,1‐b]quinazolines. These are readily cleaved under mild conditions.
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