Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions
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2012
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
Syntheses of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions incorporating heteroatom-based nucleophiles have been examined and discussed. The formation of (5,6)-membered systems was feasible with all nucleophiles tried (O, S and N), while the closing of the five-membered ring was restricted to O- and S-nucleophiles. The closure of a four-membered ring failed. Instead, the bicyclic (5,6)-membered acetal derivative and the tricyclic system with an eight-membered central ring were obtained from the substrates containing O and S nucleophilic moieties, respectively. The reaction outcome and stereochemistry are rationalized using quantum chemical calculations at B3LYP/6-31G(d) level. The exclusive cis-stereoselectivity in the formation of (5,6)- and (5,5)-membered systems results from thermodynamic control, whereas the formation of the eight-membered ring was kinetically controlled.
Izvor:
Organic & Biomolecular Chemistry, 2012, 10, 3, 575-589Izdavač:
- Royal Soc Chemistry, Cambridge
Finansiranje / projekti:
- Tiazolidni i sintetički analozi: reaktivnost, primena i biološka aktivnost (RS-MESTD-MPN2006-2010-142007)
- Deutscher Akademischer Austauschdienst (DAAD) [504 252 70]
DOI: 10.1039/c1ob06451g
ISSN: 1477-0520
PubMed: 22113469
WoS: 000298750800018
Scopus: 2-s2.0-84055214179
Institucija/grupa
IHTMTY - JOUR AU - Stojanović, Milovan AU - Marković, Rade AU - Kleinpeter, Erich AU - Baranac-Stojanović, Marija PY - 2012 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1011 AB - Syntheses of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions incorporating heteroatom-based nucleophiles have been examined and discussed. The formation of (5,6)-membered systems was feasible with all nucleophiles tried (O, S and N), while the closing of the five-membered ring was restricted to O- and S-nucleophiles. The closure of a four-membered ring failed. Instead, the bicyclic (5,6)-membered acetal derivative and the tricyclic system with an eight-membered central ring were obtained from the substrates containing O and S nucleophilic moieties, respectively. The reaction outcome and stereochemistry are rationalized using quantum chemical calculations at B3LYP/6-31G(d) level. The exclusive cis-stereoselectivity in the formation of (5,6)- and (5,5)-membered systems results from thermodynamic control, whereas the formation of the eight-membered ring was kinetically controlled. PB - Royal Soc Chemistry, Cambridge T2 - Organic & Biomolecular Chemistry T1 - Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions VL - 10 IS - 3 SP - 575 EP - 589 DO - 10.1039/c1ob06451g ER -
@article{ author = "Stojanović, Milovan and Marković, Rade and Kleinpeter, Erich and Baranac-Stojanović, Marija", year = "2012", abstract = "Syntheses of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions incorporating heteroatom-based nucleophiles have been examined and discussed. The formation of (5,6)-membered systems was feasible with all nucleophiles tried (O, S and N), while the closing of the five-membered ring was restricted to O- and S-nucleophiles. The closure of a four-membered ring failed. Instead, the bicyclic (5,6)-membered acetal derivative and the tricyclic system with an eight-membered central ring were obtained from the substrates containing O and S nucleophilic moieties, respectively. The reaction outcome and stereochemistry are rationalized using quantum chemical calculations at B3LYP/6-31G(d) level. The exclusive cis-stereoselectivity in the formation of (5,6)- and (5,5)-membered systems results from thermodynamic control, whereas the formation of the eight-membered ring was kinetically controlled.", publisher = "Royal Soc Chemistry, Cambridge", journal = "Organic & Biomolecular Chemistry", title = "Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions", volume = "10", number = "3", pages = "575-589", doi = "10.1039/c1ob06451g" }
Stojanović, M., Marković, R., Kleinpeter, E.,& Baranac-Stojanović, M.. (2012). Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions. in Organic & Biomolecular Chemistry Royal Soc Chemistry, Cambridge., 10(3), 575-589. https://doi.org/10.1039/c1ob06451g
Stojanović M, Marković R, Kleinpeter E, Baranac-Stojanović M. Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions. in Organic & Biomolecular Chemistry. 2012;10(3):575-589. doi:10.1039/c1ob06451g .
Stojanović, Milovan, Marković, Rade, Kleinpeter, Erich, Baranac-Stojanović, Marija, "Synthesis of thiazolidine-fused heterocycles via exo-mode cyclizations of vinylogous N-acyliminium ions" in Organic & Biomolecular Chemistry, 10, no. 3 (2012):575-589, https://doi.org/10.1039/c1ob06451g . .