Regiospecificty in the heterocyclization of β-oxonitriles to 5-substituted 4-oxothiazolidine derivatives
Regiospecifičnost u heterociklizaciji β-oksonitrilado 5-supstituisanih 4-oksotiazolidinskih derivata
Abstract
Astudy on the regiospecificity of the base-catalyzed reaction of activated β-oxonitriles 1 with diethyl mercaptosuccinate affording the title compounds 3 is reported. Other competitive heterocyclic products, that is 4-oxo-1,3-thiazinanes 4, derivatives of tetrahydrothiophene 5 and/or thiacyclohexane 6 which on the grounds of mechanistic considerations could be formed, were not observed. Spectroscopic and experimental evidence together with theoretical considerations, provides a reasonable explanation for the observed regiospecificity.
Proučavana je regiospecifičnost bazno-katalizovane reakcije aktiviranih β-oksonitrilado 1 sa dietil-estrom merkaptoćilibarne kiseline u kojoj se grade u naslovu navedena jedinjenja 3. Mogući heterociklični proizvodi 4-okso-1,3-tiazini 4, derivati tetrahidrotiofena 5 i/ili tijacikloheksana 6 koji mogu biti nagrađeni na osnovu mehanističkog razmatranja, nisu detektovani. Spektroskopski i eksperimentalni dokazi sa teorijskim obrazloženjem daju prihvatljivo objašnjenje za uočenu regiospecifičnost.
Keywords:
regiospecific / heterocyclization / 4-oxothiazolidinesSource:
Journal of the Serbian Chemical Society, 2003, 68, 4-5, 383-390Publisher:
- Serbian Chemical Society
DOI: 10.2298/JSC0305383M
ISSN: 0352-5139
WoS: 000183423800016
Scopus: 2-s2.0-0038173387
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Institution/Community
IHTMTY - JOUR AU - Marković, Rade AU - Džambaski, Zdravko AU - Stojanović, Milovan AU - Steel, Peter AU - Baranac, Marija M. PY - 2003 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/114 AB - Astudy on the regiospecificity of the base-catalyzed reaction of activated β-oxonitriles 1 with diethyl mercaptosuccinate affording the title compounds 3 is reported. Other competitive heterocyclic products, that is 4-oxo-1,3-thiazinanes 4, derivatives of tetrahydrothiophene 5 and/or thiacyclohexane 6 which on the grounds of mechanistic considerations could be formed, were not observed. Spectroscopic and experimental evidence together with theoretical considerations, provides a reasonable explanation for the observed regiospecificity. AB - Proučavana je regiospecifičnost bazno-katalizovane reakcije aktiviranih β-oksonitrilado 1 sa dietil-estrom merkaptoćilibarne kiseline u kojoj se grade u naslovu navedena jedinjenja 3. Mogući heterociklični proizvodi 4-okso-1,3-tiazini 4, derivati tetrahidrotiofena 5 i/ili tijacikloheksana 6 koji mogu biti nagrađeni na osnovu mehanističkog razmatranja, nisu detektovani. Spektroskopski i eksperimentalni dokazi sa teorijskim obrazloženjem daju prihvatljivo objašnjenje za uočenu regiospecifičnost. PB - Serbian Chemical Society T2 - Journal of the Serbian Chemical Society T1 - Regiospecificty in the heterocyclization of β-oxonitriles to 5-substituted 4-oxothiazolidine derivatives T1 - Regiospecifičnost u heterociklizaciji β-oksonitrilado 5-supstituisanih 4-oksotiazolidinskih derivata VL - 68 IS - 4-5 SP - 383 EP - 390 DO - 10.2298/JSC0305383M ER -
@article{ author = "Marković, Rade and Džambaski, Zdravko and Stojanović, Milovan and Steel, Peter and Baranac, Marija M.", year = "2003", abstract = "Astudy on the regiospecificity of the base-catalyzed reaction of activated β-oxonitriles 1 with diethyl mercaptosuccinate affording the title compounds 3 is reported. Other competitive heterocyclic products, that is 4-oxo-1,3-thiazinanes 4, derivatives of tetrahydrothiophene 5 and/or thiacyclohexane 6 which on the grounds of mechanistic considerations could be formed, were not observed. Spectroscopic and experimental evidence together with theoretical considerations, provides a reasonable explanation for the observed regiospecificity., Proučavana je regiospecifičnost bazno-katalizovane reakcije aktiviranih β-oksonitrilado 1 sa dietil-estrom merkaptoćilibarne kiseline u kojoj se grade u naslovu navedena jedinjenja 3. Mogući heterociklični proizvodi 4-okso-1,3-tiazini 4, derivati tetrahidrotiofena 5 i/ili tijacikloheksana 6 koji mogu biti nagrađeni na osnovu mehanističkog razmatranja, nisu detektovani. Spektroskopski i eksperimentalni dokazi sa teorijskim obrazloženjem daju prihvatljivo objašnjenje za uočenu regiospecifičnost.", publisher = "Serbian Chemical Society", journal = "Journal of the Serbian Chemical Society", title = "Regiospecificty in the heterocyclization of β-oxonitriles to 5-substituted 4-oxothiazolidine derivatives, Regiospecifičnost u heterociklizaciji β-oksonitrilado 5-supstituisanih 4-oksotiazolidinskih derivata", volume = "68", number = "4-5", pages = "383-390", doi = "10.2298/JSC0305383M" }
Marković, R., Džambaski, Z., Stojanović, M., Steel, P.,& Baranac, M. M.. (2003). Regiospecificty in the heterocyclization of β-oxonitriles to 5-substituted 4-oxothiazolidine derivatives. in Journal of the Serbian Chemical Society Serbian Chemical Society., 68(4-5), 383-390. https://doi.org/10.2298/JSC0305383M
Marković R, Džambaski Z, Stojanović M, Steel P, Baranac MM. Regiospecificty in the heterocyclization of β-oxonitriles to 5-substituted 4-oxothiazolidine derivatives. in Journal of the Serbian Chemical Society. 2003;68(4-5):383-390. doi:10.2298/JSC0305383M .
Marković, Rade, Džambaski, Zdravko, Stojanović, Milovan, Steel, Peter, Baranac, Marija M., "Regiospecificty in the heterocyclization of β-oxonitriles to 5-substituted 4-oxothiazolidine derivatives" in Journal of the Serbian Chemical Society, 68, no. 4-5 (2003):383-390, https://doi.org/10.2298/JSC0305383M . .