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Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives
Trithiaazapentalene derivatives were prepared by the reaction of 2-alkylidene-4-oxothiazolidines with Lawesson's reagent. They are classified as two structurally different trithiaazapentalene compounds that have different contributions of monocyclic 1,2-dithiole and 1,2,4-dithiazole structures and degrees of aromaticity of the bicyclic trithiaazapentalene system. The electron-donating ability of substituents at the C(5) position of the trithiaazapentalene system is recognized as the main cause for changes in pi-Celectron distribution. This is the first complete study of substituent effects on the structure of trithiapentalenes.
Keywords:
Trithiapentalene / 1,2-Dithiole / 1,2,4-Dithiazole / 4-Oxothiazolidine / Rearrangement to trithiaazapentalene / Push-pull character
TY - JOUR
AU - Rašović, Aleksandar
AU - Koch, Andreas
AU - Kleinpeter, Erich
AU - Marković, Rade
PY - 2013
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1227
AB - Trithiaazapentalene derivatives were prepared by the reaction of 2-alkylidene-4-oxothiazolidines with Lawesson's reagent. They are classified as two structurally different trithiaazapentalene compounds that have different contributions of monocyclic 1,2-dithiole and 1,2,4-dithiazole structures and degrees of aromaticity of the bicyclic trithiaazapentalene system. The electron-donating ability of substituents at the C(5) position of the trithiaazapentalene system is recognized as the main cause for changes in pi-Celectron distribution. This is the first complete study of substituent effects on the structure of trithiapentalenes.
PB - Oxford : Pergamon-Elsevier Science Ltd
T2 - Tetrahedron
T1 - Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives
VL - 69
IS - 51
SP - 10849
EP - 10857
DO - 10.1016/j.tet.2013.10.088
ER -
@article{
author = "Rašović, Aleksandar and Koch, Andreas and Kleinpeter, Erich and Marković, Rade",
year = "2013",
abstract = "Trithiaazapentalene derivatives were prepared by the reaction of 2-alkylidene-4-oxothiazolidines with Lawesson's reagent. They are classified as two structurally different trithiaazapentalene compounds that have different contributions of monocyclic 1,2-dithiole and 1,2,4-dithiazole structures and degrees of aromaticity of the bicyclic trithiaazapentalene system. The electron-donating ability of substituents at the C(5) position of the trithiaazapentalene system is recognized as the main cause for changes in pi-Celectron distribution. This is the first complete study of substituent effects on the structure of trithiapentalenes.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives",
volume = "69",
number = "51",
pages = "10849-10857",
doi = "10.1016/j.tet.2013.10.088"
}
Rašović, A., Koch, A., Kleinpeter, E.,& Marković, R.. (2013). Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 69(51), 10849-10857.
https://doi.org/10.1016/j.tet.2013.10.088
Rašović A, Koch A, Kleinpeter E, Marković R. Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives. in Tetrahedron. 2013;69(51):10849-10857.
doi:10.1016/j.tet.2013.10.088 .
Rašović, Aleksandar, Koch, Andreas, Kleinpeter, Erich, Marković, Rade, "Studies of the regioselective ring-opening closing mode of functionally different thiazolidine type enaminones: en route to the synthesis of trithiaazapentalene derivatives" in Tetrahedron, 69, no. 51 (2013):10849-10857,
https://doi.org/10.1016/j.tet.2013.10.088 . .
