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Different Modes of Acid-Promoted Cyclooligomerization of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered versus 28-Membered Polyazamacrocycle Formation
[Image: see text] Unprecedented self-assembly of a novel 14-membered cyclic bis-thiosemicarbazone or/and a 28-membered cyclic tetrakis-thiosemicarbazone upon acid-promoted cyclooligomerization of 4-(4-thiosemicarbazido)butan-2-one hydrazone has been discovered. A thorough study of the influence of v...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9724087/ https://www.ncbi.nlm.nih.gov/pubmed/36383744 http://dx.doi.org/10.1021/acs.joc.2c01199 |
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author | Fesenko, Anastasia A. Grigoriev, Mikhail S. Arion, Vladimir B. Shutalev, Anatoly D. |
author_facet | Fesenko, Anastasia A. Grigoriev, Mikhail S. Arion, Vladimir B. Shutalev, Anatoly D. |
author_sort | Fesenko, Anastasia A. |
collection | PubMed |
description | [Image: see text] Unprecedented self-assembly of a novel 14-membered cyclic bis-thiosemicarbazone or/and a 28-membered cyclic tetrakis-thiosemicarbazone upon acid-promoted cyclooligomerization of 4-(4-thiosemicarbazido)butan-2-one hydrazone has been discovered. A thorough study of the influence of various factors on the direction of macrocyclization provided the optimal conditions for the highly selective formation of each of the macrocycles in excellent yields. Plausible pathways for macrocyclizations have been discussed. The macrocycle precursor was prepared by the reaction of readily available 4-isothiocyanatobutan-2-one with an excess of hydrazine. |
format | Online Article Text |
id | pubmed-9724087 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-97240872022-12-07 Different Modes of Acid-Promoted Cyclooligomerization of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered versus 28-Membered Polyazamacrocycle Formation Fesenko, Anastasia A. Grigoriev, Mikhail S. Arion, Vladimir B. Shutalev, Anatoly D. J Org Chem [Image: see text] Unprecedented self-assembly of a novel 14-membered cyclic bis-thiosemicarbazone or/and a 28-membered cyclic tetrakis-thiosemicarbazone upon acid-promoted cyclooligomerization of 4-(4-thiosemicarbazido)butan-2-one hydrazone has been discovered. A thorough study of the influence of various factors on the direction of macrocyclization provided the optimal conditions for the highly selective formation of each of the macrocycles in excellent yields. Plausible pathways for macrocyclizations have been discussed. The macrocycle precursor was prepared by the reaction of readily available 4-isothiocyanatobutan-2-one with an excess of hydrazine. American Chemical Society 2022-11-16 2022-12-02 /pmc/articles/PMC9724087/ /pubmed/36383744 http://dx.doi.org/10.1021/acs.joc.2c01199 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Fesenko, Anastasia A. Grigoriev, Mikhail S. Arion, Vladimir B. Shutalev, Anatoly D. Different Modes of Acid-Promoted Cyclooligomerization of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered versus 28-Membered Polyazamacrocycle Formation |
title | Different Modes of Acid-Promoted
Cyclooligomerization
of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered
versus 28-Membered Polyazamacrocycle Formation |
title_full | Different Modes of Acid-Promoted
Cyclooligomerization
of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered
versus 28-Membered Polyazamacrocycle Formation |
title_fullStr | Different Modes of Acid-Promoted
Cyclooligomerization
of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered
versus 28-Membered Polyazamacrocycle Formation |
title_full_unstemmed | Different Modes of Acid-Promoted
Cyclooligomerization
of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered
versus 28-Membered Polyazamacrocycle Formation |
title_short | Different Modes of Acid-Promoted
Cyclooligomerization
of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered
versus 28-Membered Polyazamacrocycle Formation |
title_sort | different modes of acid-promoted
cyclooligomerization
of 4-(4-thiosemicarbazido)butan-2-one hydrazone: 14-membered
versus 28-membered polyazamacrocycle formation |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9724087/ https://www.ncbi.nlm.nih.gov/pubmed/36383744 http://dx.doi.org/10.1021/acs.joc.2c01199 |
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