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Synthesis of novel 14-membered cyclic bis-semicarbazones |
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| Authors: | Anatoly D. Shutalev Anastasia A. Fesenko Olesya M. Kuzmina Alexander N. Volov Dmitry V. Albov Vladimir V. Chernyshev Ilia A. Zamilatskov |
| Affiliation: | 1. Department of Organic Chemistry, Moscow State University of Fine Chemical Technologies, 86 Vernadsky Avenue, 119571 Moscow, Russian Federation;2. A. N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS, 31 Leninsky Prospect, 119071 Moscow, Russian Federation;3. Department of Chemistry, M. V. Lomonosov Moscow State University, 1-3 Leninskie Gory, 119991 Moscow, Russian Federation |
| Abstract: | 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. |
| Keywords: | CIRSUKQCGDSERL-UHFFFAOYSA-N PTMFSFDKAHDLKQ-UHFFFAOYSA-N CEJZGXMUQGETID-UHFFFAOYSA-N MTGPLHSHAPABFE-UHFFFAOYSA-N UFRUXCJMYHRLCH-OVCLIPMQSA-N MEUNWPREWOMOEY-CXUHLZMHSA-N CZISUPBEWROIHZ-RYQLWAFASA-N WXAJODSWXCLNTC-XUIWWLCJSA-N |
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