Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones
Tionovanje n-metil- i n-nesupstituisanih tiazolidinonskih enaminona
2004
Autori
Marković, RadeRašović, Aleksandar
Baranac, Marija M.
Stojanović, Milovan
Steel, Peter
Jovetić, Stanka L.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
The potential of directional non-bonded 1,5-type S···O interactions to initiate the incipient stage of an in situ rearrangement of N-unsubstituted thiazolidine enaminones to functionalized 1,2-dithioles has been demonstrated. The spectral characteristics, as well as X-ray structural analysis of a selected rearranged product, indicate that a dynamic interconversion occurs in solution between the 1,2-dithiole and the 3,3aλ4,4-trithia-1-azapentalene bicylic form. The lack of the rearrangement in the case of a N-methyl substituted enaminone precursor is attributed to an unfavorable methyl migration in the last reaction step.
Pokazan je potencijal usmerenih nevezivnih interakcija 1,5-tipa S···O da iniciraju početnu fazu in situ premeštanja N-nesupstituisanih tiazolidinonskih enaminona u funkcionalizovane 1,2-ditiole. Spektralne karakteristike, kao i kristalografska strukturna analiza izabranog premeštenog proizvoda, ukazuju na brzu interkonverziju između 1,2-ditiola i 3, 3aλ4,4-tritija-1-azapentalenskog bicikličnog oblika. Odsustvo premeštanja u slučaju N-metil-supstituisanog enaminomskog prekursora pripisano je nefavorizovanom premeštanju metil-grupe u završnoj fazi reakcije.
Ključne reči:
thiazolidine / enaminone / Lawesson’s reagent / 1,2-dithiole / 3 / 3aλ4,4-trithiaIzvor:
Journal of the Serbian Chemical Society, 2004, 69, 11, 909-918Izdavač:
- Serbian Chemical Society
Finansiranje / projekti:
- Project MESTD, br. 1709
DOI: 10.2298/JSC0411909M
ISSN: 0352-5139
WoS: 000226120300010
Scopus: 2-s2.0-31544465959
Institucija/grupa
IHTMTY - JOUR AU - Marković, Rade AU - Rašović, Aleksandar AU - Baranac, Marija M. AU - Stojanović, Milovan AU - Steel, Peter AU - Jovetić, Stanka L. PY - 2004 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/139 AB - The potential of directional non-bonded 1,5-type S···O interactions to initiate the incipient stage of an in situ rearrangement of N-unsubstituted thiazolidine enaminones to functionalized 1,2-dithioles has been demonstrated. The spectral characteristics, as well as X-ray structural analysis of a selected rearranged product, indicate that a dynamic interconversion occurs in solution between the 1,2-dithiole and the 3,3aλ4,4-trithia-1-azapentalene bicylic form. The lack of the rearrangement in the case of a N-methyl substituted enaminone precursor is attributed to an unfavorable methyl migration in the last reaction step. AB - Pokazan je potencijal usmerenih nevezivnih interakcija 1,5-tipa S···O da iniciraju početnu fazu in situ premeštanja N-nesupstituisanih tiazolidinonskih enaminona u funkcionalizovane 1,2-ditiole. Spektralne karakteristike, kao i kristalografska strukturna analiza izabranog premeštenog proizvoda, ukazuju na brzu interkonverziju između 1,2-ditiola i 3, 3aλ4,4-tritija-1-azapentalenskog bicikličnog oblika. Odsustvo premeštanja u slučaju N-metil-supstituisanog enaminomskog prekursora pripisano je nefavorizovanom premeštanju metil-grupe u završnoj fazi reakcije. PB - Serbian Chemical Society T2 - Journal of the Serbian Chemical Society T1 - Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones T1 - Tionovanje n-metil- i n-nesupstituisanih tiazolidinonskih enaminona VL - 69 IS - 11 SP - 909 EP - 918 DO - 10.2298/JSC0411909M ER -
@article{ author = "Marković, Rade and Rašović, Aleksandar and Baranac, Marija M. and Stojanović, Milovan and Steel, Peter and Jovetić, Stanka L.", year = "2004", abstract = "The potential of directional non-bonded 1,5-type S···O interactions to initiate the incipient stage of an in situ rearrangement of N-unsubstituted thiazolidine enaminones to functionalized 1,2-dithioles has been demonstrated. The spectral characteristics, as well as X-ray structural analysis of a selected rearranged product, indicate that a dynamic interconversion occurs in solution between the 1,2-dithiole and the 3,3aλ4,4-trithia-1-azapentalene bicylic form. The lack of the rearrangement in the case of a N-methyl substituted enaminone precursor is attributed to an unfavorable methyl migration in the last reaction step., Pokazan je potencijal usmerenih nevezivnih interakcija 1,5-tipa S···O da iniciraju početnu fazu in situ premeštanja N-nesupstituisanih tiazolidinonskih enaminona u funkcionalizovane 1,2-ditiole. Spektralne karakteristike, kao i kristalografska strukturna analiza izabranog premeštenog proizvoda, ukazuju na brzu interkonverziju između 1,2-ditiola i 3, 3aλ4,4-tritija-1-azapentalenskog bicikličnog oblika. Odsustvo premeštanja u slučaju N-metil-supstituisanog enaminomskog prekursora pripisano je nefavorizovanom premeštanju metil-grupe u završnoj fazi reakcije.", publisher = "Serbian Chemical Society", journal = "Journal of the Serbian Chemical Society", title = "Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones, Tionovanje n-metil- i n-nesupstituisanih tiazolidinonskih enaminona", volume = "69", number = "11", pages = "909-918", doi = "10.2298/JSC0411909M" }
Marković, R., Rašović, A., Baranac, M. M., Stojanović, M., Steel, P.,& Jovetić, S. L.. (2004). Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones. in Journal of the Serbian Chemical Society Serbian Chemical Society., 69(11), 909-918. https://doi.org/10.2298/JSC0411909M
Marković R, Rašović A, Baranac MM, Stojanović M, Steel P, Jovetić SL. Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones. in Journal of the Serbian Chemical Society. 2004;69(11):909-918. doi:10.2298/JSC0411909M .
Marković, Rade, Rašović, Aleksandar, Baranac, Marija M., Stojanović, Milovan, Steel, Peter, Jovetić, Stanka L., "Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones" in Journal of the Serbian Chemical Society, 69, no. 11 (2004):909-918, https://doi.org/10.2298/JSC0411909M . .