Collect. Czech. Chem. Commun. 2002, 67, 365-372

A Facile Route to the 6-Hetaryl Substituted Pyrrolo[1,2-a]thieno[3,2-e]pyrimidine Derivatives

Yulian M. Volovenko, Elizaveta V. Resnyanska* and Anton V. Tverdokhlebov

Kiev National Taras Shevchenko University, 01033, Volodimirska str., 62, Kiev, Ukraine


Hitherto unknown 6-hetaryl-4,5,7,8-tetrahydropyrrolo[1,2-a]thieno[3,2-e]pyrimidine-4,7-diones (7a-7g) were prepared by reaction of ethyl 2-aminothiophene-3-carboxylates 5 with 4-chloro-2-hetaryl-3-oxobutanonitriles 4 in DMF at 100 °C. When the same reagents were treated in the presence of triethylamine, a dependence of the reaction pathway on the nature of the hetaryl substituent in chloronitrile component was observed. This was explained in terms of steric factors.

Keywords: Nitrogen heterocycles; Pyrrolo[1,2-a]thieno[3,2-e]pyrimidines; Thiophenes; 2-Aminothiophene-3-carboxylates; 4-Chloro-2-hetaryl-3-oxobutanonitriles; Heterocyclization.

References: 35 live references.