Error message

  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).

Synthesis of Annelated P- and N-containing Heterocycles Based on Methyl 5-Aminothiophene-2-Carboxylate Derivatives

Svitlana Kovaleva, Olena Mayboroda, Natalia Simurova, Larysa Mazur
Affiliation: 
National University of Food Technologies 68, Volodymyrska St., 01601 Kyiv, Ukraine sval_kov@ukr.net
DOI: 
https://doi.org/10.23939/chcht13.02.145
AttachmentSize
PDF icon full_text.pdf116.77 KB

Keywords:

Abstract: 
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.
References: 

[1] Mathey F.: Phosphorus-Carbon Heterocyclic Chemistry. Pergamon Press, Oxford 2001.
[2] Ishii A., Yoshioka R., Nakayama J., Hoshino M.: 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., Bergmans W., Karpati T. et al.: Chem.-Eur. J., 2005, 11, 4687. https://doi.org/10.1002/chem.200500152
[8] Ishii A., Takaki I., Nakayama J., Hoshino M.: 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., Heymann M., 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., Hoshino M.: Tetrahedron Lett., 1993, 34, 2347.
https://doi.org/10.1016/S0040-4039(00)77610-6
[13] Ishii A., Takaki I., Nakayama J., Hoshino M.: Tetrahedron Lett., 1993, 34, 8255.
https://doi.org/10.1016/S0040-4039(00)61404-1
[14] Ishii A., Yoshioka R„ Nakayama J., Hoshino M.: 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., Vargaus M.: 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.