401647-91-4Relevant articles and documents
Synthesis of novel 14-membered cyclic bis-semicarbazones
Shutalev, Anatoly D.,Fesenko, Anastasia A.,Kuzmina, Olesya M.,Volov, Alexander N.,Albov, Dmitry V.,Chernyshev, Vladimir V.,Zamilatskov, Ilia A.
, p. 5481 - 5485 (2014)
An efficient method for the stereoselective synthesis of novel 14-membered cyclic bis-semicarbazones based on acid-catalyzed cyclization of the hydrazones of 3-(3-oxobutyl)semicarbazides has been developed. The starting semicarbazides were prepared according to a four-step strategy involving amidoalkylation of the sodium enolate of acetylacetone with N-(α-tosylbenzyl)carbamates followed by base-promoted retro-Claisen reaction and treatment of the obtained N-(3-oxobutyl)carbamates with hydrazine.
Different modes of acid-catalyzed cyclization of 4-(γ-oxoalkyl)semicarbazide hydrazones: 7-membered versus 14-membered cyclic semicarbazones formation
Fesenko, Anastasia A.,Shutalev, Anatoly D.
, p. 9528 - 9543 (2015/12/05)
Acid-catalyzed cyclization of 4-(γ-oxoalkyl)semicarbazide hydrazones has been studied. 7-Membered cyclic semicarbazones, 2,4,5,6-tetrahydro-3H-1,2,4-triazepin-3-ones, were obtained from the γ-phenyl-substituted semicarbazides, while the cyclization of the γ-methyl-substituted semicarbazides involved two molecules of the starting material to result in 14-membered cyclic bis-semicarbazones, 1,2,4,8,9,11-hexaazacyclotetradeca-7,14-diene-3,10-diones. The 4-(γ-oxoalkyl)semicarbazide hydrazones were prepared according to a four-step synthesis based on amidoalkylation of the sodium enolates of 1,3-diketones with ethyl N-(1-tosylalk-1-yl)carbamates followed by base-promoted retro-Claisen reaction and treatment of the obtained ethyl N-(γ-oxoalkyl)carbamates with hydrazine.