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Paper | Regular issue | Vol 91, No. 1, 2015, pp.64-75
Published online, 25th December, 2014
DOI: 10.3987/COM-14-13135
Reaction of 2-Chloro-1-alkyl-1H-Indol-3-carbaldehydes with Barbituric Acids and 5-Methyl-2-phenyl-2,4-dihydropyrazol-3-one. Formation of Compound with Extremely Short Intramolecular Hydrogen Bond in Eight-Membered Pseudocycle

Konstantin F. Suzdalev,* Maria N. Babakova, Victor G. Kartsev, and Konstantin A. Krasnov

*Department of Chemistry, Southern Federal University, Zorge Street 7, Rostov-on-Don, 344090, Russia


New indolin-2-one derivatives, containing in its molecules eight-membered pseudo-cycle with unusually short intramolecular hydrogen bond in OHO-bridge have been synthesized by reaction of 2-chloro-1-alkyl-1H-indole-3-carbaldehyde with barbituric acids or 5-methyl-2-phenyl-2,4-dihydropyrazol-3-one. Under the action of amines they undergo fragmentation to 5-aminomethylenebarbituric acids or 4-aminomethylenepyrazolones and 1-alkyl-1,3-dihydroindol-2-ones.