Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5221045 | Tetrahedron | 2012 | 9 Pages |
Electrocatalytic assembling of aldehydes and N,Nâ²-dialkylbarbituric acids leads to selective and efficient formation of substituted 1,5-dihydro-2H,2â²H-spiro[furo[2,3-d]pyrimidine-6,5â²-pyrimidine]-2,2â²,4,4â²,6â²-(1â²H,3H,3â²H)-pentones in 70-85% yields as a result of the complex cascade process. The electrocatalytic process smoothly proceeds with aromatic aldehydes bearing both electron-donating and electron-withdrawing groups, and allows for the selective and efficient one-step formation of spirobarbiturates containing furo[2,3-d]pyrimidine scaffold, which are a perspective class of compounds with prominent pharmacological and physiological activity. The application of the effective electrocatalytic cascade method to the formation of medicinally relevant spiro[furo[2,3-d]pyrimidine-6,5â²-pyrimidine]-2,2â²,4,4â²,6â²-(1â²H,3H,3â²H)-pentones is also beneficial from the viewpoint of diversity-oriented large-scale processes and represents a novel, facile and environmentally benign synthetic concept for electrocatalytic cascade reaction strategy.
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