Regiospecificity in the heterocyclization of b-oxonitriles to 5-substituted 4-oxothiazolidine derivatives
A study on the regiospecificity of the base-catalyzed reaction of activated b-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 thiacyclohexan...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2003-05-01
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| Series: | Journal of the Serbian Chemical Society |
| Subjects: | |
| Online Access: | http://www.shd.org.yu/HtDocs/SHD/Vol68/No4-5/V68-No4_5-15.pdf |
| _version_ | 1828377696165429248 |
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| author | PETER STEEL MARIJA BARANAC MILOVAN STOJANOVIC ZDRAVKO DZAMBASKI RADE MARKOVIC |
| author_facet | PETER STEEL MARIJA BARANAC MILOVAN STOJANOVIC ZDRAVKO DZAMBASKI RADE MARKOVIC |
| author_sort | PETER STEEL |
| collection | DOAJ |
| description | A study on the regiospecificity of the base-catalyzed reaction of activated b-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. |
| first_indexed | 2024-04-14T08:16:03Z |
| format | Article |
| id | doaj.art-026c6e0721224a9e99383397850ef402 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 |
| language | English |
| last_indexed | 2024-04-14T08:16:03Z |
| publishDate | 2003-05-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-026c6e0721224a9e99383397850ef4022022-12-22T02:04:23ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51392003-05-01684-5383390Regiospecificity in the heterocyclization of b-oxonitriles to 5-substituted 4-oxothiazolidine derivativesPETER STEELMARIJA BARANACMILOVAN STOJANOVICZDRAVKO DZAMBASKIRADE MARKOVICA study on the regiospecificity of the base-catalyzed reaction of activated b-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.http://www.shd.org.yu/HtDocs/SHD/Vol68/No4-5/V68-No4_5-15.pdfregiospecificheterocyclization4-oxothiazolidines |
| spellingShingle | PETER STEEL MARIJA BARANAC MILOVAN STOJANOVIC ZDRAVKO DZAMBASKI RADE MARKOVIC Regiospecificity in the heterocyclization of b-oxonitriles to 5-substituted 4-oxothiazolidine derivatives Journal of the Serbian Chemical Society regiospecific heterocyclization 4-oxothiazolidines |
| title | Regiospecificity in the heterocyclization of b-oxonitriles to 5-substituted 4-oxothiazolidine derivatives |
| title_full | Regiospecificity in the heterocyclization of b-oxonitriles to 5-substituted 4-oxothiazolidine derivatives |
| title_fullStr | Regiospecificity in the heterocyclization of b-oxonitriles to 5-substituted 4-oxothiazolidine derivatives |
| title_full_unstemmed | Regiospecificity in the heterocyclization of b-oxonitriles to 5-substituted 4-oxothiazolidine derivatives |
| title_short | Regiospecificity in the heterocyclization of b-oxonitriles to 5-substituted 4-oxothiazolidine derivatives |
| title_sort | regiospecificity in the heterocyclization of b oxonitriles to 5 substituted 4 oxothiazolidine derivatives |
| topic | regiospecific heterocyclization 4-oxothiazolidines |
| url | http://www.shd.org.yu/HtDocs/SHD/Vol68/No4-5/V68-No4_5-15.pdf |
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