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pi-Annulation reactions of 4-thiazolidinone enaminones in the synthesis of fused bi- and tri-cyclic compounds

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2012
Authors
Bondžić, Bojan
Džambaski, Zdravko
Bondžić, Aleksandra M.
Marković, Rade
Article (Published version)
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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 olefins
Source:
Tetrahedron, 2012, 68, 47, 9556-9565
Publisher:
  • Pergamon-Elsevier Science Ltd, Oxford
Projects:
  • Experimental and theoretical study of reactivity and biological activity of stereodefined thiazolidines and their synthetic analogues (RS-172020)

DOI: 10.1016/j.tet.2012.09.080

ISSN: 0040-4020

WoS: 000310402400004

Scopus: 2-s2.0-84867509791
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/1126
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