Balbi A, Roma G, Mazzei M, Sottofattori E, Cadel S, Schiantarelli P
Istituto di Scienze Farmaceutiche, Università di Genova.
Farmaco. 1989 Jun;44(6):565-77.
Substituted 2-(dialkylamino)-3-formylchromones (II) were obtained from the reaction of substituted 2-(dialkylamino)chromones (I) either with the N,N-dimethylformamide-POCl3 reagent [compounds (IIa-e)] or with dichloromethylmethylether in the presence of TiCl4 [compounds (IIf-i)]. By treating (IIa,f) with hydroxylamine the oximes (IIIa,f) were prepared, which in turn were converted into the nitriles (IVa,f) by treatment with acetic anhydride. Compound (IIa), selected for the smallest steric hindrance of the 2-dialkylamino substituent, by reaction with hydrazines afforded [1]benzopyrano [2,3-c]pyrazole derivatives (VI), whereas reaction of (IIa) with guanidine, benzamidine or S-methylisothiourea gave rise to the formation of 5H-[1]benzopyrano[2,3-d]pyrimidine derivatives (IX). Among the compounds tested for their antiallergic properties, (IIf) showed an appreciable activity, but also high toxicity.
取代的2-(二烷基氨基)-3-甲酰基色酮（II）是由取代的2-(二烷基氨基)色酮（I）与N,N-二甲基甲酰胺-POCl₃试剂[化合物（IIa - e）]或在TiCl₄存在下与二氯甲基甲基醚反应[化合物（IIf - i）]制得的。通过用羟胺处理（IIa,f）制备了肟（IIIa,f），然后用乙酸酐处理将其转化为腈（IVa,f）。选择具有最小空间位阻的2-二烷基氨基取代基的化合物（IIa），通过与肼反应得到[1]苯并吡喃并[2,3 - c]吡唑衍生物（VI），而（IIa）与胍、苯甲脒或S-甲基异硫脲反应则生成5H-[1]苯并吡喃并[2,3 - d]嘧啶衍生物（IX）。在测试其抗过敏特性的化合物中，（IIf）表现出可观的活性，但毒性也很高。
