Sadek E. Abdou

Activated nitriles in heterocyclic synthesis: Synthesis of several new coumarin derivatives

Several new benzopyran and benzopyranopyridine derivatives were synthesized via condensation of 2-amino-1,1,3-tricyanopropene (1) and diethyl 2-amino-1-cyanopropene-1,3-dicarboxylate (2) with salicylaldehyde and treatment of the resulted products with active methylene regents. The spectroscopic data of the synthesized compounds are reported and discussed.ZusammenfassungEinige neue Benzopyran- und Benzopyranopyridin-derivate wurden durch Kondensation von 2-Amino-1,1,3-tricyanopropen (1) und 2-Amino-1-cyanopropen-1,3-dicarbonsäuredimethylester (2) mit Salicylaldehyd und Behandlung der Reaktionsprodukte mit aktiven Methylenreagenzien dargestellt. Die spektroskopischen Daten der neuen Verbindungen werden diskutiert.

REACTIONS WITH HYDRAZIDOYL HALIDES. IX: A NOVEL SYNTHESIS OF SOME HYDRAZIDOYL SULFIDES, THIADIAZOLINES,THIAZOLES AND COUMARINES

Abstract The reactions of hydrazidoyl halides with N-phenylcyanothioacetamide and α-cyanothioacetamide gave unexpected hydrazidoyl sulfides, thiadiazolines and thiazole derivatives. The structures of these products were confirmed by elemental analyses and spectral data and wherever possible, alternate synthesis.

Synthesis of several new isoxazole, imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, benzoxadiazine and benzothiazine derivatives from hydroximoyl halides

Furoylhydroximoyl chloride3 reacted with 2-aminopyridine, 2-aminopyrimidine,O-aminophenol,O-phenylenediamine and aminothiophenol to afford imidazo[1,2-a]pyridine6, imidazo[1,2-a]pyrimidine8, benzoxadiazine10, nitrosobenzopyrazine13a and nitrosobenzothiazine13b, respectively. Isoxazoline18 and pyrrolidino[3,4-d]isoxazolin-4,6-dione derivatives19a and19b obtained by the reaction of3 with acrylonitrile and N-arylmaleimide. Hydroximoyl chloride3 reacted with thiophenol and sodium benzenesulfinate to yield furylglyoxaloxime16a and16b, respectively. Hydroximoyl chloride3 reacted also with some active methylene compound to give isoxazole derivatives20–23, respectively.