Quinazolines. VIII. Synthesis of 1,3‐diaminobenzo[f]quinazolines
Quinazolines. VIII. Synthesis of 1,3‐diaminobenzo[f]quinazolines
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VIII. 1,3-二氨基苯并[f]喹唑啉的合成
DOI：
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发表时间：
1972
期刊：
影响因子：
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通讯作者：
E. Modest
中科院分区：
文献类型：
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作者：
A. Rosowsky;Katherine K. N. Chen;Marilyn E. Nadel;N. Papathanasopoulos;E. Modest
Twenty-one 1,3-diaminobenzo[f]quinazolines (2, R = H, alkyl, halogen, methoxy) were synthesized as planar tricyclic analogs of the antimalarial agent pyrimethamine (1). The synthetic methods included i) condensation of 1-cyano-2-naphthylamines with cyanamide in the presence of pyridine hydrochloride, ii) cyclization of N1,N5-bis(2-naphthyl)biguanide hydrochlorides in diphenyl ether at 250°, iii) reaction of 2-naphthylamine hydrochlorides with excess sodium dicyanamide in boiling 1-octanol, and iv) selenium dioxide dehydrogenation of 1,3-diamino-5,6-dihydrobenzo[f]quinazolines. A number of new 2-naphthols and 2-naphthylamines were synthesized as intermediates. Substituent effects on the ultraviolet absorption spectra of 1,3-diamino-benzo[f]quinazolines were investigated and found to be additive. These compounds are of interest as inhibitors of dihydrofolate reductase and as potential antimalarial and antitumor agents.
