Reactions of some quinazoline compounds with ethoxymethylenemalonic acid derivatives
作者:
Leslie W. Deady,
Maureen F. Mackay,
Dianne M. Werden,
期刊:
Journal of Heterocyclic Chemistry
(WILEY Available online 1989)
卷期:
Volume 26,
issue 1
页码: 161-168
ISSN:0022-152X
年代: 1989
DOI:10.1002/jhet.5570260129
出版商: Wiley‐Blackwell
数据来源: WILEY
摘要:
AbstractThe reactions of ethyl (1,4‐dihydro‐4‐oxoquinazolin‐2‐yl)acetate4and 2‐aminoquinazolin‐4(1H)‐one5with 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 readil
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