A general and stereoselective approach to 14-membered cyclic bis-semicarbazones involving BF3-catalyzed amidoalkylation of 2-(trimethylsilyloxy)propene

A general and stereoselective five-step approach to 14-membered cyclic bis-semicarbazones, 5,12-diaryl-7,14-dimethyl-1,2,4,8,9,11-hexaazacyclotetradeca-7,14-diene-3,10-diones, starting from aldehyde semicarbazones has been developed. The key intermediates, 4-(3-oxobut-1-yl)semicarbazones, were prepa...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-06, Vol.20 (22), p.4569-4588
Main Authors: Fesenko, Anastasia A, Shutalev, Anatoly D
Format: Article
Language:English
Subjects:
Aldehydes
Aromatic compounds
Hydrazine
Hydrazines
Hydrazones
Intermediates
Stereoselectivity
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Summary:A general and stereoselective five-step approach to 14-membered cyclic bis-semicarbazones, 5,12-diaryl-7,14-dimethyl-1,2,4,8,9,11-hexaazacyclotetradeca-7,14-diene-3,10-diones, starting from aldehyde semicarbazones has been developed. The key intermediates, 4-(3-oxobut-1-yl)semicarbazones, were prepared by BF3-catalyzed amidoalkylation of 2-(trimethylsilyloxy)propene with 4-[(aryl)(methoxy)methyl]- or 4-[(aryl)(tosyl)methyl]semicarbazones. Treatment of these intermediates with excess of hydrazine gave hydrazones of 4-(3-oxobut-1-yl)semicarbazones or 4-(3-oxobut-1-yl)semicarbazides, which in the presence of TsOH were converted into the target macrocycles. All steps of this approach could be scaled up easily to the multi-gram level.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00644h