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Chemistry and pharmacology of pyrane derivatives. XVII. Synthesis of substituted 2- (dialkylamino) -3-formylchromones and their tricyclic derivatives

Balbi, A.; Roma, G.; Mazzei, M.; Sottofattori, E.; Cadel, S.; Schiantarelli, P.

Farmaco 44(6): 565-577

1989

ISSN/ISBN: 0014-827X
PMID: 2803447
Document Number: 345657
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.

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