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Thionation of N-methyl- and N-unsubstituted thiazolidine enaminones

Tionovanje n-metil- i n-nesupstituisanih tiazolidinonskih enaminona

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2004
137.pdf (152.0Kb)
Authors
Marković, Rade
Rašović, Aleksandar
Baranac, Marija M.
Stojanović, Milovan
Steel, Peter
Jovetić, Stanka L.
Article (Published version)
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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.
Keywords:
thiazolidine / enaminone / Lawesson’s reagent / 1,2-dithiole / 3 / 3aλ4,4-trithia
Source:
Journal of the Serbian Chemical Society, 2004, 69, 11, 909-918
Publisher:
  • Serbian Chemical Society
Projects:
  • Project MESTD, br. 1709

DOI: 10.2298/JSC0411909M

ISSN: 0352-5139

WoS: 000226120300010

Scopus: 2-s2.0-31544465959
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/139
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