Synthesis of novel 14-membered cyclic bis-semicarbazones

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 amidoal...

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Bibliographic Details
Published inTetrahedron letters Vol. 55; no. 40; pp. 5481 - 5485
Main Authors Shutalev, Anatoly D., Fesenko, Anastasia A., Kuzmina, Olesya M., Volov, Alexander N., Albov, Dmitry V., Chernyshev, Vladimir V., Zamilatskov, Ilia A.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.10.2014
Elsevier
Subjects
Amidoalkylation
Azamacrocycles
Chemistry
Chemistry, Organic
Cyclic semicarbazones
Physical Sciences
retro-Claisen reaction
Science & Technology
Semicarbazides
CEJZGXMUQGETID-UHFFFAOYSA-N
Amidoalkylation
MTGPLHSHAPABFE-UHFFFAOYSA-N
Cyclic semicarbazones
CIRSUKQCGDSERL-UHFFFAOYSA-N
retro-Claisen reaction
Semicarbazides
UFRUXCJMYHRLCH-OVCLIPMQSA-N
Azamacrocycles
CZISUPBEWROIHZ-RYQLWAFASA-N
MEUNWPREWOMOEY-CXUHLZMHSA-N
PTMFSFDKAHDLKQ-UHFFFAOYSA-N
WXAJODSWXCLNTC-XUIWWLCJSA-N
TRIAZOLINONE DERIVATIVES
TRIAZOLONE
COMPLEXES
II RECEPTOR ANTAGONISTS
ALDEHYDES
AZA-MICHAEL REACTIONS
BETA-AMINO KETONES
MANNICH REACTIONS
CONDENSATION
AGENTS
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Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.08.016