https://oldena.lpnu.ua/handle/ntb/46469| Title: | Synthesis of Annelated P- and N-containing Heterocycles Based on Methyl 5-Aminothiophene-2-Carboxylate Derivatives |
| Other Titles: | Синтез анельованих гетероциклів, що містять P- і N-атоми, на основі похідних 5-аміно-2-метоксикарбонілтіофену |
| Authors: | Kovaleva, Svitlana Mayboroda, Olena Simurova, Natalia Mazur, Larysa |
| Affiliation: | National University of Food Technologies |
| Bibliographic description (Ukraine): | Synthesis of Annelated P- and N-containing Heterocycles Based on Methyl 5-Aminothiophene-2-Carboxylate Derivatives / Svitlana Kovaleva, Olena Mayboroda, Natalia Simurova, Larysa Mazur // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2019. — Vol 13. — No 2. — P. 145–149. |
| Bibliographic description (International): | Synthesis of Annelated P- and N-containing Heterocycles Based on Methyl 5-Aminothiophene-2-Carboxylate Derivatives / Svitlana Kovaleva, Olena Mayboroda, Natalia Simurova, Larysa Mazur // Chemistry & Chemical Technology. — Lviv : Lviv Politechnic Publishing House, 2019. — Vol 13. — No 2. — P. 145–149. |
| Is part of: | Chemistry & Chemical Technology, 2 (13), 2019 |
| Issue: | 2 |
| Issue Date: | 28-Feb-2019 |
| Publisher: | Видавництво Львівської політехніки Lviv Politechnic Publishing House |
| Place of the edition/event: | Львів Lviv |
| Keywords: | тіофен азафосфінін оксазафосфінін анельовані цикли гетероцикл фосфорилювання thiophene azaphosphinine oxazaphosphinine fused rings heterocycle phosphorylation |
| Number of pages: | 5 |
| Page range: | 145-149 |
| Start page: | 145 |
| End page: | 149 |
| Abstract: | Синтезовані похідні нових біциклічних
систем – 1H-тієно[3,2-c][1,5,2]оксазофосфініну і 1,2-дігідро-
тієно[2,3-b][1,4] азафосфініну за реакцією фосфорилювання N-
заміщених похідних 2-аміно-5-метоксикарбонілтіофену з
трибромідом фосфору(III). Показано, що гетероциклізація
може бути проведена в основному середовищі і за м'яких умов.
Методами хімічного аналізу, 1H і 31P ЯМР спектроскопії
вивчено кінцеві продукти реакції. Derivatives of new bicyclic systems – 1H-thieno[3,2-c][1,5,2]oxazaphosphinine and 1,2-dihydrothieno[ 2,3-b][1,4]azaphosphinine have been obtained by phosphorylation of N-substituted derivatives of 5-amino- 2-methoxycarbonylthiophene with phosphorus (III) tribromide. These heterocyclizations can be carried out in the basic medium and under mild conditions. The end reaction products were studied by means of chemical analysis, 1H and 31P NMR spectroscopy. |
| URI: | https://ena.lpnu.ua/handle/ntb/46469 |
| Copyright owner: | © Національний університет „Львівська політехніка“, 2019 © Kovaleva S., Mayboroda O., Simurova N., Mazur L., 2019 |
| URL for reference material: | https://doi.org/10.1016/S0040-4039(00)61405-3 https://doi.org/10.1002/hc.21163 https://doi.org/10.1039/C2JM33526C https://doi.org/10.1002/chem.200700399 https://doi.org/10.1021/ol052911p https://doi.org/10.1002/chem.200500152 https://doi.org/10.1080/10426509308045639 https://doi.org/10.3987/COM-97-7930 https://doi.org/10.1002/cber.19761090137 https://doi.org/10.1016/S0022-328X(00)93116-4 https://doi.org/10.1016/S0040-4039(00)77610-6 https://doi.org/10.1016/S0040-4039(00)61404-1 https://doi.org/10.1080/10426509608054662 https://doi.org/10.3987/COM-97-7911 https://doi.org/10.1016/S0040-4020(01)87270-7 https://doi.org/10.1139/V09-108 https://doi.org/10.1002/asia.201000196 https://doi.org/10.1080/03086648208073110 https://doi.org/10.1002/zaac.19774370107 |
| References (Ukraine): | 1. Mathey F.: Phosphorus-Carbon Heterocyclic Chemistry. Pergamon Press, Oxford 2001. 2. Ishii A., Yoshioka R., Nakayama J., HoshinoM.: Tetrahedron Lett., 1993, 34, 8259. https://doi.org/10.1016/S0040-4039(00)61405-3 3. Uchiyama Y., Kawaguchi T., Kuroda K.: Heteroatom. Chem., 2014, 25, 326. https://doi.org/10.1002/hc.21163 4. Kondo R., Yasuda T., Yang Y., Kim J. Y., Adachi C.: J. Mater. Chem., 2012, 22, 16810. https://doi.org/10.1039/C2JM33526C 5. Dienes Y., Durben S., Karpati T. et al.: Chem.-Eur. J., 2007, 13, 7487. https://doi.org/10.1002/chem.200700399 6. Neumann T., Dienes Y., Baumgartner T.: Org. Lett., 2006, 8, 495. https://doi.org/10.1021/ol052911p 7. Baumgartner T., BergmansW., Karpati T. et al.: Chem.-Eur. J., 2005, 11, 4687. https://doi.org/10.1002/chem.200500152 8. Ishii A., Takaki I., Nakayama J., HoshinoM.: Phosphorus Sulfur, 1993, 77, 149. https://doi.org/10.1080/10426509308045639 9. Yasuike S., Nakashima F, Kurita J., Tsuchiya T.: Heterocycles, 1997, 45, 1899. https://doi.org/10.3987/COM-97-7930 10. Fenske D., Longer K., HeymannM., Becher H.-J.: Chem. Ber., 1976, 109, 359. https://doi.org/10.1002/cber.19761090137 11. Lampin J., Mathey F.: J. Organomet. Chem., 1974, 71, 239. https://doi.org/10.1016/S0022-328X(00)93116-4 12. Ishii A., Tsuchiya Т., Nakayama J., HoshinoM.: Tetrahedron Lett., 1993, 34, 2347. https://doi.org/10.1016/S0040-4039(00)77610-6 13. Ishii A., Takaki I., Nakayama J., HoshinoM.: Tetrahedron Lett., 1993, 34, 8255. https://doi.org/10.1016/S0040-4039(00)61404-1 14. Ishii A., Yoshioka R„ Nakayama J., HoshinoM.: Tetrahedron Lett., 1993, 34, 8259. https://doi.org/10.1016/S0040-4039(00)61405-3 15. Combes C., Plenat F., Cristau H.-J.: Phosphorus, Sulfur, Silicon. Relat. Elem., 1996, 111, 33. https://doi.org/10.1080/10426509608054662 16. Yasuike S., Nakashima F., Kurita J., Tsuchiya T.: Heterocycles, 1997, 45, 1899. https://doi.org/10.3987/COM-97-7930 17. Yasuike S., Kurita J., Tsuchiya T.: Heterocycles, 1997, 45, 1891. https://doi.org/10.3987/COM-97-7911 18. Dotz K., Tiriliomis A., Harms K.: Tetrahedron, 1993, 49, 5577. https://doi.org/10.1016/S0040-4020(01)87270-7 19. Ren Y., Linder T., Baumgartner T.: Can. J. Chem., 2009, 87, 1222. https://doi.org/10.1139/V09-108 20. Ren Y., Baumgartner T.: Chem.-Asian J., 2010, 5, 1918. https://doi.org/10.1002/asia.201000196 21. Kovaleva S., Chubaruk N., Tolmachov A., Pinchuk A.: Khim. Heterocycl. Soed., 2001, 9, 1287. 22. Kovaleva S., Simurova N., Mayboroda E.: Ukr. Khim. Zh., 2016, 82, 91. 23. Schmidpeter A., Gross J., Schrenk E., Sheldrick N.: Phosphorus Sulfur, 1982, 14, 49. https://doi.org/10.1080/03086648208073110 24. Fluck E., VargausM.: Zeitschrift für anorganische und allgemeine Chemie., 1977, 437, 53. https://doi.org/10.1002/zaac.19774370107 25. Volochnuk D., Pushechnikov A., Krotko D. et al.: Synthesis, 2003, 6, 906. |
| References (International): | 1. Mathey F., Phosphorus-Carbon Heterocyclic Chemistry. Pergamon Press, Oxford 2001. 2. Ishii A., Yoshioka R., Nakayama J., HoshinoM., Tetrahedron Lett., 1993, 34, 8259. https://doi.org/10.1016/S0040-4039(00)61405-3 3. Uchiyama Y., Kawaguchi T., Kuroda K., Heteroatom. Chem., 2014, 25, 326. https://doi.org/10.1002/hc.21163 4. Kondo R., Yasuda T., Yang Y., Kim J. Y., Adachi C., J. Mater. Chem., 2012, 22, 16810. https://doi.org/10.1039/P.2JM33526C 5. Dienes Y., Durben S., Karpati T. et al., Chem.-Eur. J., 2007, 13, 7487. https://doi.org/10.1002/chem.200700399 6. Neumann T., Dienes Y., Baumgartner T., Org. Lett., 2006, 8, 495. https://doi.org/10.1021/ol052911p 7. Baumgartner T., BergmansW., Karpati T. et al., Chem.-Eur. J., 2005, 11, 4687. https://doi.org/10.1002/chem.200500152 8. Ishii A., Takaki I., Nakayama J., HoshinoM., Phosphorus Sulfur, 1993, 77, 149. https://doi.org/10.1080/10426509308045639 9. Yasuike S., Nakashima F, Kurita J., Tsuchiya T., Heterocycles, 1997, 45, 1899. https://doi.org/10.3987/COM-97-7930 10. Fenske D., Longer K., HeymannM., Becher H.-J., Chem. Ber., 1976, 109, 359. https://doi.org/10.1002/cber.19761090137 11. Lampin J., Mathey F., J. Organomet. Chem., 1974, 71, 239. https://doi.org/10.1016/S0022-328X(00)93116-4 12. Ishii A., Tsuchiya T., Nakayama J., HoshinoM., Tetrahedron Lett., 1993, 34, 2347. https://doi.org/10.1016/S0040-4039(00)77610-6 13. Ishii A., Takaki I., Nakayama J., HoshinoM., Tetrahedron Lett., 1993, 34, 8255. https://doi.org/10.1016/S0040-4039(00)61404-1 14. Ishii A., Yoshioka R" Nakayama J., HoshinoM., Tetrahedron Lett., 1993, 34, 8259. https://doi.org/10.1016/S0040-4039(00)61405-3 15. Combes C., Plenat F., Cristau H.-J., Phosphorus, Sulfur, Silicon. Relat. Elem., 1996, 111, 33. https://doi.org/10.1080/10426509608054662 16. Yasuike S., Nakashima F., Kurita J., Tsuchiya T., Heterocycles, 1997, 45, 1899. https://doi.org/10.3987/COM-97-7930 17. Yasuike S., Kurita J., Tsuchiya T., Heterocycles, 1997, 45, 1891. https://doi.org/10.3987/COM-97-7911 18. Dotz K., Tiriliomis A., Harms K., Tetrahedron, 1993, 49, 5577. https://doi.org/10.1016/S0040-4020(01)87270-7 19. Ren Y., Linder T., Baumgartner T., Can. J. Chem., 2009, 87, 1222. https://doi.org/10.1139/V09-108 20. Ren Y., Baumgartner T., Chem.-Asian J., 2010, 5, 1918. https://doi.org/10.1002/asia.201000196 21. Kovaleva S., Chubaruk N., Tolmachov A., Pinchuk A., Khim. Heterocycl. Soed., 2001, 9, 1287. 22. Kovaleva S., Simurova N., Mayboroda E., Ukr. Khim. Zh., 2016, 82, 91. 23. Schmidpeter A., Gross J., Schrenk E., Sheldrick N., Phosphorus Sulfur, 1982, 14, 49. https://doi.org/10.1080/03086648208073110 24. Fluck E., VargausM., Zeitschrift für anorganische und allgemeine Chemie., 1977, 437, 53. https://doi.org/10.1002/zaac.19774370107 25. Volochnuk D., Pushechnikov A., Krotko D. et al., Synthesis, 2003, 6, 906. |
| Content type: | Article |
| Appears in Collections: | Chemistry & Chemical Technology. – 2019. – Vol. 13, No. 2 |
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