Issue 22, 2022

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
05 Apr 2022
Accepted
11 May 2022
First published
11 May 2022

Org. Biomol. Chem., 2022,20, 4569-4588

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

A. A. Fesenko and A. D. Shutalev, Org. Biomol. Chem., 2022, 20, 4569 DOI: 10.1039/D2OB00644H

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