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New pyrazolothienopyrimidines were synthesized. The key intermediate 4-aminothieno[2,3- c ]pyrazole-5-carbonitrile  1  was converted to the chloroacetyl amino derivative  2  followed by nucleophilic substitution and Dimorth rearrangement upon treatment with nitrogen nucleophiles to give the pyrimidinones  3a-c . Treatment of  3a  with formaldehyde and with triethyl orthoformate afforded the respective tetracyclic derivatives  4  and  5 . Condensation of the amino group in the  o -aminocarbonitrile  1  with triethyl orthoformate followed by cycloaddition reaction with hydrazine led to the formation of pyrazolothienopyrimidine  8 . Compound  8  was used as a synthetic precursor to heterocyclic compounds comprised of pyrazole, triazole, triazine, and triazepine derivatives.

Efficient synthesis, reactions and spectral characterization of pyrazolo[4’,3’:4,5]thieno[3,2- d ] pyrimidines and related heterocycles