pi-Annulation reactions of 4-thiazolidinone enaminones in the synthesis of fused bi- and tri-cyclic compounds
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.
Keywords:
Thiazolidinones / pi-Annulation / Iminium cyclizations / Enaminones / Push-pull olefinsSource:
Tetrahedron, 2012, 68, 47, 9556-9565Publisher:
- Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
- Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-MESTD-Basic Research (BR or ON)-172020)
DOI: 10.1016/j.tet.2012.09.080
ISSN: 0040-4020
WoS: 000310402400004
Scopus: 2-s2.0-84867509791
Collections
Institution/Community
IHTMTY - JOUR AU - Bondžić, Bojan AU - Džambaski, Zdravko AU - Bondžić, Aleksandra M. AU - Marković, Rade PY - 2012 UR - https://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 - Oxford : Pergamon-Elsevier Science Ltd 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", 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 = "Oxford : Pergamon-Elsevier Science Ltd", 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. in Tetrahedron Oxford : Pergamon-Elsevier Science Ltd., 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. in Tetrahedron. 2012;68(47):9556-9565. doi:10.1016/j.tet.2012.09.080 .
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" in Tetrahedron, 68, no. 47 (2012):9556-9565, https://doi.org/10.1016/j.tet.2012.09.080 . .