Electrochemically induced multicomponent assembling of isatins, 4-hydroxyquinolin-2(1H)-one and malononitrile: a convenient and efficient way to functionalized spirocyclic [indole-3,4'-pyrano[3,2-c]quinoline] scaffold.
Electrochemically induced catalytic multicomponent transformation of isatins, 4-hydroxyquinolin-2(1H)-one and malononitrile in ethanol in an undivided cell in the presence of sodium bromide as an electrolyte results in the formation of spirooxindoles with fused functionalized indole-3,4'-pyrano[3,2-c]quinoline] scaffold in 75-91% substance yields and 500-600% current yield. The developed efficient electrocatalytic approach to medicinally relevant [indole-3,4'-pyrano[3,2-c]quinoline] scaffold is beneficial from the viewpoint of diversity-oriented large-scale processes and represents a novel example of facile environmentally benign synthetic concept for electrocatalytic multicomponent reactions.
Elinson
Michail N
MN
N. D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, 119991, Moscow, Russia. elinson@ioc.ac.ru
Merkulova
Valentina M
VM
Ilovaisky
Alexey I
AI
Demchuk
Dmitry V
DV
Belyakov
Pavel A
PA
Nikishin
Gennady I
GI
D002384:Catalysis; D003500:Cyclization; D004526:Efficiency; D055664:Electrochemical Techniques / Q000379:methods*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D006912:Hydroxyquinolines / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D046911:Macromolecular Substances / Q000138:chemical synthesis* / Q000737:chemistry; D008954:Models, Biological; D009570:Nitriles / Q000737:chemistry*; D015363:Quinolones / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry
D006571:Heterocyclic Compounds; D006912:Hydroxyquinolines; D007211:Indoles; D046911:Macromolecular Substances; D009570:Nitriles; D015363:Quinolones; D013141:Spiro Compounds; D007510:Isatin; C000945:dicyanmethane; C034010:4-hydroxyquinoline