Electrocatalytic and chemical assembling of N, N′-dialkylbarbituric acids and aldehydes: efficient cascade approach to the spiro-[furo[2,3- d]pyrimidine-6,5′-pyrimidine]-2,2′,4,4′,6′-(1′ H,3 H,3′ H)-pentone framework

• Published in: Tetrahedron Vol. 68; no. 4; pp. 1198 - 1206
• Main Authors: Vereshchagin, Anatolii N., Elinson, Michail N., Dorofeeva, Evgeniya O., Zaimovskaya, Tatiana A., Stepanov, Nikita O., Gorbunov, Sergey V., Belyakov, Pavel A., Nikishin, Gennady I.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 28.01.2012; Elsevier
• Subjects: Aldehydes; Aromatic compounds; Assembling; Barbiturates; Bearing; Cascade reactions; Cascades; Chemistry; Chemistry, Organic; Electrocatalysis; Formations; Physical Sciences; Science & Technology; Spirofuropyrimidines; Strategy; Tetrahedrons; Spirofuropyrimidines; Electrocatalysis; Barbiturates; Aldehydes; Cascade reactions; PRIVILEGED STRUCTURES; ONE-POT SYNTHESIS; MALONATE; DRUG DISCOVERY; ANTICONVULSANT; SUBSTITUTED CYCLOPROPANES; MULTICOMPONENT REACTIONS; ELECTROCHEMICAL TRANSFORMATION; MALONONITRILE; CHEMISTRY
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2011.11.057

Electrocatalytic assembling of aldehydes and N, N′-dialkylbarbituric acids leads to selective and efficient formation of substituted 1,5-dihydro-2 H,2′ H-spiro[furo[2,3- d]pyrimidine-6,5′-pyrimidine]-2,2′,4,4′,6′-(1′ H,3 H,3′ H)-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-6,5′-pyrimidine]-2,2′,4,4′,6′-(1′ H,3 H,3′ H)-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. [Display omitted]