The a-C position in 4-oxo thiazolidinones functions as one of the three possible nucleophilic sites in these molecules. We used the inherent reactivity of alpha-C of the exocyclic double bond (a so called push pull system) to obtain bicyclic fused thiazolidinones via pi-annulation cyclization. Appropriate reaction conditions to selectively activate this position and secondary nitrogen towards N, pi-annulation were found. Furthermore, the intramolecular vinylogous iminium ion 6-exo-trig cyclization was used to access fused bicyclic precursors for the pi-annulation in order to obtain the novel tricyclic structures stereoselectively.
TY - JOUR
AU - Bondžić, Bojan
AU - Džambaski, Zdravko
AU - Bondžić, Aleksandra M.
AU - Marković, Rade
PY - 2012
UR - http://cer.ihtm.bg.ac.rs/handle/123456789/1126
AB - The a-C position in 4-oxo thiazolidinones functions as one of the three possible nucleophilic sites in these molecules. We used the inherent reactivity of alpha-C of the exocyclic double bond (a so called push pull system) to obtain bicyclic fused thiazolidinones via pi-annulation cyclization. Appropriate reaction conditions to selectively activate this position and secondary nitrogen towards N, pi-annulation were found. Furthermore, the intramolecular vinylogous iminium ion 6-exo-trig cyclization was used to access fused bicyclic precursors for the pi-annulation in order to obtain the novel tricyclic structures stereoselectively.
PB - Pergamon-Elsevier Science Ltd, Oxford
T2 - Tetrahedron
T1 - pi-Annulation reactions of 4-thiazolidinone enaminones in the synthesis of fused bi- and tri-cyclic compounds
VL - 68
IS - 47
SP - 9556
EP - 9565
DO - 10.1016/j.tet.2012.09.080
ER -
@article{
author = "Bondžić, Bojan and Džambaski, Zdravko and Bondžić, Aleksandra M. and Marković, Rade",
year = "2012",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/1126",
abstract = "The a-C position in 4-oxo thiazolidinones functions as one of the three possible nucleophilic sites in these molecules. We used the inherent reactivity of alpha-C of the exocyclic double bond (a so called push pull system) to obtain bicyclic fused thiazolidinones via pi-annulation cyclization. Appropriate reaction conditions to selectively activate this position and secondary nitrogen towards N, pi-annulation were found. Furthermore, the intramolecular vinylogous iminium ion 6-exo-trig cyclization was used to access fused bicyclic precursors for the pi-annulation in order to obtain the novel tricyclic structures stereoselectively.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "pi-Annulation reactions of 4-thiazolidinone enaminones in the synthesis of fused bi- and tri-cyclic compounds",
volume = "68",
number = "47",
pages = "9556-9565",
doi = "10.1016/j.tet.2012.09.080"
}
Bondžić, B., Džambaski, Z., Bondžić, A. M.,& Marković, R. (2012). pi-Annulation reactions of 4-thiazolidinone enaminones in the synthesis of fused bi- and tri-cyclic compounds.
Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 68(47), 9556-9565.
https://doi.org/10.1016/j.tet.2012.09.080
Bondžić B, Džambaski Z, Bondžić AM, Marković R. pi-Annulation reactions of 4-thiazolidinone enaminones in the synthesis of fused bi- and tri-cyclic compounds. Tetrahedron. 2012;68(47):9556-9565
Bondžić Bojan, Džambaski Zdravko, Bondžić Aleksandra M., Marković Rade, "pi-Annulation reactions of 4-thiazolidinone enaminones in the synthesis of fused bi- and tri-cyclic compounds" Tetrahedron, 68, no. 47 (2012):9556-9565,
https://doi.org/10.1016/j.tet.2012.09.080 .
