l-Proline-Catalyzed Cyclization of 6-Aminopyrimidine-4(3H)-ones with Nitroolefins: Synthesis of Polysubstituted 5-Arylpyrrolo[2,3-d]pyrimidin-4-ones

Abstract

A simple and efficient one-pot procedure for the synthesis of new pyrrolo[2,3-d]pyrimidine derivatives has been established through an l-proline-catalyzed cyclization of 6-aminopyrimidine-4(3H)-one with nitroolefins in water. The reaction at 80 °C in water gives various highly substituted pyrrolo[2,3-d]pyrimidines in good to excellent yields. This procedure has the advantages of environmental friendliness, good yields, and convenient operation.

Aminouracil and aminothiouracil as versatile precursors for a variety of heterocyclic systems

“…Scheme 13. Synthesis of tetrakis(6-aminopyrimidine-2,4(1H,3H)-dione) derivatives 30a-h. 77 revealed the synthesis of pyrrolo [2,3-d]pyrimidin-4-ones 32a-f via reaction of nitroolefins 31 with 6-aminopyrimidinedione derivatives 3 or 6 using L-proline as an acid catalyst (Scheme 14, Table 3). Scheme 14.…”