Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones
Tionovanje n-metil- i n-nesupstituisanih tiazolidinonskih enaminona
2004
Аутори
Marković, R.Rašović, Aleksandar
Baranac-Stojanović, Marija
Stojanović, Milovan
Steel, PJ
Jovetic, S
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
The potential of directional non-bonded 1,5-type (SO)-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 3,3alambda(4),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.
Кључне речи:
thiazolidine / enaminone / enaminone / Lawesson's reagent / Lawesson’s reagent / 1,2-dithiole / 1,2-dithiole / 3 / 3,3a lambda(4) / 4-trithia-1-azapentalene / 3aλ4,4-trithiaИзвор:
Journal of the Serbian Chemical Society, 2004, 69, 11, 909-918Издавач:
- Serbian Chemical Soc, Belgrade
DOI: 10.2298/JSC0411909M
ISSN: 0352-5139
WoS: 000226120300010
Scopus: 2-s2.0-31544465959
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Marković, R. AU - Rašović, Aleksandar AU - Baranac-Stojanović, Marija AU - Stojanović, Milovan AU - Steel, PJ AU - Jovetic, S PY - 2004 UR - https://cherry.chem.bg.ac.rs/handle/123456789/679 AB - The potential of directional non-bonded 1,5-type (SO)-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 3,3alambda(4),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 Soc, Belgrade 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, R. and Rašović, Aleksandar and Baranac-Stojanović, Marija and Stojanović, Milovan and Steel, PJ and Jovetic, S", year = "2004", abstract = "The potential of directional non-bonded 1,5-type (SO)-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 3,3alambda(4),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 Soc, Belgrade", 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-Stojanović, M., Stojanović, M., Steel, P.,& Jovetic, S.. (2004). Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones. in Journal of the Serbian Chemical Society Serbian Chemical Soc, Belgrade., 69(11), 909-918. https://doi.org/10.2298/JSC0411909M
Marković R, Rašović A, Baranac-Stojanović M, Stojanović M, Steel P, Jovetic S. 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, R., Rašović, Aleksandar, Baranac-Stojanović, Marija, Stojanović, Milovan, Steel, PJ, Jovetic, S, "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 . .