Electrocatalytic tandem Knoevenagel–Michael addition of barbituric acids to isatins: Facile and efficient way to substituted 5,5′-(2-oxo-2,3-dihydro-1H-indole-3,3-diyl)bis(pyrimidine-2,4,6-(1H,3H,5H)-trione) scaffold

Electrocatalytic tandem Knoevenagel–Michael addition of barbituric acids to isatins: Facile and efficient way to substituted 5,5′-(2-oxo-2,3-dihydro-1H-indole-3,3-diyl)bis(pyrimidine-2,4,6-(1H,3H,5H)-trione) scaffold Full article

Journal

Electrochimica Acta
ISSN: 1873-3859 , E-ISSN: 0013-4686

Output data

Year: 2011, Volume: 56, Number: 24, Pages: 8219-8223 Pages count : 5 DOI: 10.1016/j.electacta.2011.06.059

Authors

Elinson Michail N. ¹ , Merkulova Valentina M. ¹ , Ilovaisky Alexey I. ¹ , Barba Fructuoso ² , Batanero Belen ²

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russia
2	Department of Organic Chemistry, University of Alcalá, 28871 Alcalá de Henares, Madrid, Spain

Electrocatalytic transformation of isatins and barbituric acids in ethanol in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of substituted 5,5′-(2-oxo-2,3-dihydro-1H-indole-3,3-diyl)bis(pyrimidine-2,4,6(1H,3H,5H)-triones) in 89–95% substance yields and 890–950% current yields. The developed efficient electrocatalytic approach to medicinally relevant 5,5′-(2-oxo-2,3-dihydro-1H-indole-3,3-diyl)bis(pyrimidine-2,4,6(1H,3H,5H)-trione) scaffold is 10 times faster than general chemical method, is beneficial from the viewpoint of diversity-oriented large-scale processes and represents novel example of facile environmentally benign synthetic concept for electrocatalytic tandem reaction strategy.

Elinson M.N. , Merkulova V.M. , Ilovaisky A.I. , Barba F. , Batanero B.
Electrocatalytic tandem Knoevenagel–Michael addition of barbituric acids to isatins: Facile and efficient way to substituted 5,5′-(2-oxo-2,3-dihydro-1H-indole-3,3-diyl)bis(pyrimidine-2,4,6-(1H,3H,5H)-trione) scaffold
Electrochimica Acta. 2011. V.56. N24. P.8219-8223. DOI: 10.1016/j.electacta.2011.06.059 WOS Scopus OpenAlex

Web of science:	WOS:000295601600017
Scopus:	2-s2.0-80052799304
OpenAlex:	W2041238765

DB	Citing
OpenAlex	41
Scopus	43
Web of science	46