Summary
Phenylsulfonylacetophenones1 react with a mixture of elemental sulfur and malononitrile to yield the corresponding 2-amino-4-aryl-5-phenylsulfonylthiophene-3-carbonitriles2. Compound2a could be annelated to the corresponding thieno[2,3-d]pyrimidine and thieno[2,3-c]-pyrazole derivatives3 and5 upon reaction with nitrogen nucleophiles (cyanamide and hydroxylamine hydrochloride), respectively. The applicability and synthetic potency of5 to develop a facile convenient route to the polyfunctionally substituted thieno[2′,3′:3,4]pyrazolo[1,5-a]pyrimidines8, 14, 17, 20, and21 is reported. Chemical and spectroscopic evidences for the structures of the new compounds are presented.
Zusammenfassung
Die Phenylsulfonylacetophenone1 reagieren mit einem Gemisch aus elementarem Schwefel und Malonsäurenitril zu den entsprechenden 2-Amino-4-aryl-5-phenylsulfonylthiophen-3-carbonitrilen2. Durch Umsetzung mit Stickstoffnucleophilen wie Cyanamid und Hydroxylaminhydrochlorid konnten aus Verbindung2a die entsprechenden Thieno[2,3-d]pyrimidin- und Thieno[2,3-c]pyrazolderivate erhalten werden. Das synthetische Potential und die Anwendbarkeit von5 zur Synthese polyfunktionell substituierter Thieno[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine (8,14,17,20,21) werden beschrieben. Die Strukturen der neuen Verbindungen wurden durch chemische und spektroskopische Methoden abgesichert.
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Sherif, S.M., Hussein, A.M. Syntheses with heterocyclic β-enaminonitriles: An expeditious synthetic approach to polyfunctionally substituted 5-phenylsulfonylthiophenes and their fused derivatives. Monatsh Chem 128, 687–696 (1997). https://doi.org/10.1007/BF00807600
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DOI: https://doi.org/10.1007/BF00807600