Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones
Tionovanje n-metil- i n-nesupstituisanih tiazolidinonskih enaminona

2004
Authors
Marković, RadeRašović, Aleksandar

Baranac, Marija M.

Stojanović, Milovan

Steel, Peter

Jovetić, Stanka L.
Article (Published version)
Metadata
Show full item recordAbstract
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.
Keywords:
thiazolidine / enaminone / Lawesson’s reagent / 1,2-dithiole / 3 / 3aλ4,4-trithiaSource:
Journal of the Serbian Chemical Society, 2004, 69, 11, 909-918Publisher:
- Serbian Chemical Society
Funding / projects:
- Project MESTD, br. 1709
DOI: 10.2298/JSC0411909M
ISSN: 0352-5139
WoS: 000226120300010
Scopus: 2-s2.0-31544465959
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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 . .