Effective self-assembly of 21- and 14-membered azamacrocycles via condition-controlled cyclotrimerization or cyclodimerization of different thiosemicarbazide-based precursors
A preparative synthesis of previously unknown 21- and 14-membered azamacrocycles acid-promoted cyclotrimerization or cyclodimerization of three readily available precursors, namely, 1-amino-6-hydroxy-4,6-dimethylhexahydropyrimidine-2-thione, 4-(4-oxopent-2-yl)thiosemicarbazide hydrazone, and 5,7-dim...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2024-11, Vol.22 (46), p.9078-9093 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Fesenko, Anastasia A Grigoriev, Mikhail S Shutalev, Anatoly D |
| description | A preparative synthesis of previously unknown 21- and 14-membered azamacrocycles
acid-promoted cyclotrimerization or cyclodimerization of three readily available precursors, namely, 1-amino-6-hydroxy-4,6-dimethylhexahydropyrimidine-2-thione, 4-(4-oxopent-2-yl)thiosemicarbazide hydrazone, and 5,7-dimethyl-1,4,5,6-tetrahydro-3
-1,2,4-triazepine-3-thione has been developed. A dramatic dependence of the selectivity of macrocyclization on the reaction conditions is demonstrated. The thermodynamic aspects of the reactions are discussed based on experimental data and DFT calculation results. Plausible pathways for the formation of macrocycles are proposed. |
| doi_str_mv | 10.1039/d4ob01384k |
| format | Article |
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-1,2,4-triazepine-3-thione has been developed. A dramatic dependence of the selectivity of macrocyclization on the reaction conditions is demonstrated. The thermodynamic aspects of the reactions are discussed based on experimental data and DFT calculation results. Plausible pathways for the formation of macrocycles are proposed.</description><identifier>ISSN: 1477-0520</identifier><identifier>ISSN: 1477-0539</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d4ob01384k</identifier><identifier>PMID: 39435579</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Hydrazones ; Precursors ; Self-assembly ; Thiosemicarbazides</subject><ispartof>Organic & biomolecular chemistry, 2024-11, Vol.22 (46), p.9078-9093</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c204t-924d4612f6996702297c4f6c2fd74d0637d751e84045bff01696bea2a99518483</cites><orcidid>0000-0002-1843-3504 ; 0000-0002-8038-8230</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/39435579$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fesenko, Anastasia A</creatorcontrib><creatorcontrib>Grigoriev, Mikhail S</creatorcontrib><creatorcontrib>Shutalev, Anatoly D</creatorcontrib><title>Effective self-assembly of 21- and 14-membered azamacrocycles via condition-controlled cyclotrimerization or cyclodimerization of different thiosemicarbazide-based precursors</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>A preparative synthesis of previously unknown 21- and 14-membered azamacrocycles
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acid-promoted cyclotrimerization or cyclodimerization of three readily available precursors, namely, 1-amino-6-hydroxy-4,6-dimethylhexahydropyrimidine-2-thione, 4-(4-oxopent-2-yl)thiosemicarbazide hydrazone, and 5,7-dimethyl-1,4,5,6-tetrahydro-3
-1,2,4-triazepine-3-thione has been developed. A dramatic dependence of the selectivity of macrocyclization on the reaction conditions is demonstrated. The thermodynamic aspects of the reactions are discussed based on experimental data and DFT calculation results. Plausible pathways for the formation of macrocycles are proposed.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>39435579</pmid><doi>10.1039/d4ob01384k</doi><tpages>16</tpages><orcidid>https://orcid.org/0000-0002-1843-3504</orcidid><orcidid>https://orcid.org/0000-0002-8038-8230</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2024-11, Vol.22 (46), p.9078-9093 |
| issn | 1477-0520 1477-0539 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_3119192873 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Hydrazones Precursors Self-assembly Thiosemicarbazides |
| title | Effective self-assembly of 21- and 14-membered azamacrocycles via condition-controlled cyclotrimerization or cyclodimerization of different thiosemicarbazide-based precursors |
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