Formation of Pyrazol-1,3,4-Thiadiazoles through 1,3-Dipolar Cycloadditions of 3-Thioxo-[1,2,4]-Triazepin-5-one with Nitrilimines: An Experimental and Computational study
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Otros documentos de la autoría: Esseffar, M.; El Messaoudi, M.; Azzouzi, S.; Jalal, R.; Sáez Cases, José Antonio; Domingo, Luis R.; Latorre, J.; Liu González, M.
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comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
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Título
Formation of Pyrazol-1,3,4-Thiadiazoles through 1,3-Dipolar Cycloadditions of 3-Thioxo-[1,2,4]-Triazepin-5-one with Nitrilimines: An Experimental and Computational studyAutoría
Fecha de publicación
2009Editor
Wiley-BlackwellISSN
0894-3230Cita bibliográfica
ESSEFFAR, M., et al. Formation of pyrazol‐1, 3, 4‐thiadiazoles through 1, 3‐dipolar cycloadditions of 3‐thioxo‐[1, 2, 4]‐triazepin‐5‐one with nitrilimines: an experimental and computational study. Journal of Physical Organic Chemistry, 2009, vol. 22, no 1, p. 31-41.Tipo de documento
info:eu-repo/semantics/articleVersión de la editorial
https://onlinelibrary.wiley.com/doi/abs/10.1002/poc.1421Palabras clave / Materias
Resumen
In this work the results of experimental and computational study of the title compounds and
some ancillary compounds are reported. Two bicyclic pyrazol-1,3,4-thiadiazole derivatives
were synthesized by reaction ... [+]
In this work the results of experimental and computational study of the title compounds and
some ancillary compounds are reported. Two bicyclic pyrazol-1,3,4-thiadiazole derivatives
were synthesized by reaction between 6-dimethylaminomethylene-3-thioxo-[1,2,4]-
triazepin-5-one 1 and several nitrilimines 2a-f to give corresponding spirocycloadducts 3a-f,
which undergo a rapid rearrangement leading to the new bicyclic compounds, 4a-f and 5a-f.
These obtained bicyclic products were characterized by 1H and 13C NMR spectroscopy and
finally by X-ray crystallography. Theoretical calculations have been carried out using DFT
methods to rationalize the formation of the two new bicyclic compounds. Two reaction types
are involved in the formation of the compounds 4a-f and 5a-f. The first one is a 1,3-dipolar
cycloaddition reaction between 1 acting as dipolarophile and 2a-f as dipoles. The results
indicate that the cycloaddition between 1 and 2g, as model of 2a-c, takes place via a high
asynchronous bond-formation process. The regioselectivity obtained from the calculations is
in complete agreement with the formation of the unique spirocycloadducts 3a-f. The second
reaction leading to the formation of the final products is a domino process that is initiated by
the quick and irreversible cleavage in a catalytic acid environment of triazepenic ring. [-]
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Journal of Physical Organic Chemistry, 2009, v. 22, n. 1Derechos de acceso
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