Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/Cycloreversion
The title compounds were synthesized from C-aryl-N-methylglycines by Naroylation followed by a cyclodehydration to form the corresponding 1,3-oxazolium-5-olates. These were not isolated but converted to the title compounds by an in situ 1,3-dipolar cycloaddition/cycloreversion sequence using carbon...
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| Format: | Article |
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MDPI AG
2002-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/7/11/791/ |
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| author | Maria Joaquina Vieira Aderson de Farias Dias Alfredo Mayall Simas Joseph Miller Petrônio Filgueiras de Athayde Filho Bruno Freitas Lira |
| author_facet | Maria Joaquina Vieira Aderson de Farias Dias Alfredo Mayall Simas Joseph Miller Petrônio Filgueiras de Athayde Filho Bruno Freitas Lira |
| author_sort | Maria Joaquina Vieira |
| collection | DOAJ |
| description | The title compounds were synthesized from C-aryl-N-methylglycines by Naroylation followed by a cyclodehydration to form the corresponding 1,3-oxazolium-5-olates. These were not isolated but converted to the title compounds by an in situ 1,3-dipolar cycloaddition/cycloreversion sequence using carbon disulphide. We have studied the cyclodehydration step using acetic anhydride, trifluoroacetic anhydride and 1,3-dicyclohexylcarbodiimide (DCC) at temperatures not exceding 60oC. Trifluroacetic anhydride proved to be the best reagent, giving a better yield and more easily purified products, although yields were also acceptable with the other two reagents. |
| first_indexed | 2024-12-21T16:02:45Z |
| format | Article |
| id | doaj.art-b424b92097fb4db7840f3bec2aaac0b6 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-21T16:02:45Z |
| publishDate | 2002-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b424b92097fb4db7840f3bec2aaac0b62022-12-21T18:57:58ZengMDPI AGMolecules1420-30492002-11-0171179180010.3390/71100791Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/CycloreversionMaria Joaquina VieiraAderson de Farias DiasAlfredo Mayall SimasJoseph MillerPetrônio Filgueiras de Athayde FilhoBruno Freitas LiraThe title compounds were synthesized from C-aryl-N-methylglycines by Naroylation followed by a cyclodehydration to form the corresponding 1,3-oxazolium-5-olates. These were not isolated but converted to the title compounds by an in situ 1,3-dipolar cycloaddition/cycloreversion sequence using carbon disulphide. We have studied the cyclodehydration step using acetic anhydride, trifluoroacetic anhydride and 1,3-dicyclohexylcarbodiimide (DCC) at temperatures not exceding 60oC. Trifluroacetic anhydride proved to be the best reagent, giving a better yield and more easily purified products, although yields were also acceptable with the other two reagents.http://www.mdpi.com/1420-3049/7/11/791/Mesoionic 13-thiazolium-5-thiolatesSynthesisCharacterization |
| spellingShingle | Maria Joaquina Vieira Aderson de Farias Dias Alfredo Mayall Simas Joseph Miller Petrônio Filgueiras de Athayde Filho Bruno Freitas Lira Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/Cycloreversion Molecules Mesoionic 1 3-thiazolium-5-thiolates Synthesis Characterization |
| title | Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/Cycloreversion |
| title_full | Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/Cycloreversion |
| title_fullStr | Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/Cycloreversion |
| title_full_unstemmed | Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/Cycloreversion |
| title_short | Synthesis and Characterization of some New Mesoionic 1,3-Thiazolium-5-thiolates via Cyclodehydration and in situ 1,3-Dipolar Cycloaddition/Cycloreversion |
| title_sort | synthesis and characterization of some new mesoionic 1 3 thiazolium 5 thiolates via cyclodehydration and in situ 1 3 dipolar cycloaddition cycloreversion |
| topic | Mesoionic 1 3-thiazolium-5-thiolates Synthesis Characterization |
| url | http://www.mdpi.com/1420-3049/7/11/791/ |
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