Privileged medicinal scaffolds based on the structures of adenine-like and hypoxanthine-like pyrrolo[2,3-d]pyrimidines were prepared via one-pot four component reactions of structurally diverse aldehydes, N-(methanesulfonamido)acetophenones and malononitrile (cyanoacetamide). In preparation of the adenine-like compounds the forth component was formamide, whereas for the synthesis hypoxanthine-like compounds ethyl orthoformate was used. Both procedures are high yielding and lead to the preparation of libraries of diversely substituted medicinally relevant pyrrolo[2,3-d]pyrimidine scaffolds. Investigation of the reaction scope reveals that various aliphatic, aromatic and heteroaromatic moieties can be utilized in both the aldehyde and sulfonamidomethylaryl(hetaryl) ketone components.

Four component reactions for the synthesis of adenine-like and hypoxanthine-like pyrrolo[2,3-d]pyrimidines

243rd National Meeting (2012)

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