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Intramolecular Transformations of 3-Cyanoamino- and 3-Cyanoimino-1,2-diferrocenylcyclopropenes

3-Cyanoamino-1,2- and -2,3-diferrocenylcyclopropenes 6a,b and 11a,b prepared by the reaction of diferrocenylcyclopropenylium salts with sodium cyanamide undergo smooth intramolecular transformations with both conservation of the three-membered ring [affording 3-cyanoimino-1,2-diferrocenylcyclopropen...

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Autores principales: Klimova, Elena Ivanovna, Klimova, Tatiana, Flores-Alamo, Marcos, Backinowsky, Leon Vladimirovich, Garcia, Marcos Martinez
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6255448/
https://www.ncbi.nlm.nih.gov/pubmed/19783915
http://dx.doi.org/10.3390/molecules14093161
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author Klimova, Elena Ivanovna
Klimova, Tatiana
Flores-Alamo, Marcos
Backinowsky, Leon Vladimirovich
Garcia, Marcos Martinez
author_facet Klimova, Elena Ivanovna
Klimova, Tatiana
Flores-Alamo, Marcos
Backinowsky, Leon Vladimirovich
Garcia, Marcos Martinez
author_sort Klimova, Elena Ivanovna
collection PubMed
description 3-Cyanoamino-1,2- and -2,3-diferrocenylcyclopropenes 6a,b and 11a,b prepared by the reaction of diferrocenylcyclopropenylium salts with sodium cyanamide undergo smooth intramolecular transformations with both conservation of the three-membered ring [affording 3-cyanoimino-1,2-diferrocenylcyclopropene (8)] and its opening [affording Z-3-morpholino- and Z-3-piperidino-3-(cyanoimino)-1,2-diferrocenylprop-1-enes 7a,b and Z-3-cyanoimino-2,3-diferrocenyl-1-methylthioprop-1-ene(10)]. 3-Cyano-imino-1,2-diferrocenylcyclopropene (8) reacts with hydrazine to form 3-amino-6-ferrocenyl-5-ferrocenylmethyl-1,2,4-triazine (12) and Z-2,3-diferrocenylacrylohydrazide N-cyanoimide (13) as a result of intramolecular transformations. The structures of the compounds obtained were determined by IR, (1)H- and (13)C-NMR spectroscopy and mass spectrometry. The structures of compounds 7a and 10 were additionally confirmed by their X-ray diffraction analysis data.
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spelling pubmed-62554482018-11-30 Intramolecular Transformations of 3-Cyanoamino- and 3-Cyanoimino-1,2-diferrocenylcyclopropenes Klimova, Elena Ivanovna Klimova, Tatiana Flores-Alamo, Marcos Backinowsky, Leon Vladimirovich Garcia, Marcos Martinez Molecules Article 3-Cyanoamino-1,2- and -2,3-diferrocenylcyclopropenes 6a,b and 11a,b prepared by the reaction of diferrocenylcyclopropenylium salts with sodium cyanamide undergo smooth intramolecular transformations with both conservation of the three-membered ring [affording 3-cyanoimino-1,2-diferrocenylcyclopropene (8)] and its opening [affording Z-3-morpholino- and Z-3-piperidino-3-(cyanoimino)-1,2-diferrocenylprop-1-enes 7a,b and Z-3-cyanoimino-2,3-diferrocenyl-1-methylthioprop-1-ene(10)]. 3-Cyano-imino-1,2-diferrocenylcyclopropene (8) reacts with hydrazine to form 3-amino-6-ferrocenyl-5-ferrocenylmethyl-1,2,4-triazine (12) and Z-2,3-diferrocenylacrylohydrazide N-cyanoimide (13) as a result of intramolecular transformations. The structures of the compounds obtained were determined by IR, (1)H- and (13)C-NMR spectroscopy and mass spectrometry. The structures of compounds 7a and 10 were additionally confirmed by their X-ray diffraction analysis data. Molecular Diversity Preservation International 2009-08-26 /pmc/articles/PMC6255448/ /pubmed/19783915 http://dx.doi.org/10.3390/molecules14093161 Text en © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Klimova, Elena Ivanovna
Klimova, Tatiana
Flores-Alamo, Marcos
Backinowsky, Leon Vladimirovich
Garcia, Marcos Martinez
Intramolecular Transformations of 3-Cyanoamino- and 3-Cyanoimino-1,2-diferrocenylcyclopropenes
title Intramolecular Transformations of 3-Cyanoamino- and 3-Cyanoimino-1,2-diferrocenylcyclopropenes
title_full Intramolecular Transformations of 3-Cyanoamino- and 3-Cyanoimino-1,2-diferrocenylcyclopropenes
title_fullStr Intramolecular Transformations of 3-Cyanoamino- and 3-Cyanoimino-1,2-diferrocenylcyclopropenes
title_full_unstemmed Intramolecular Transformations of 3-Cyanoamino- and 3-Cyanoimino-1,2-diferrocenylcyclopropenes
title_short Intramolecular Transformations of 3-Cyanoamino- and 3-Cyanoimino-1,2-diferrocenylcyclopropenes
title_sort intramolecular transformations of 3-cyanoamino- and 3-cyanoimino-1,2-diferrocenylcyclopropenes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6255448/
https://www.ncbi.nlm.nih.gov/pubmed/19783915
http://dx.doi.org/10.3390/molecules14093161
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