Synthesis of heterocyclic phosphonato esters by reaction between triphenyl phosphite and acetylenic diesters in the presence of sulfur-containing heterocyclic compounds

Journal of Sulfur Chemistry

Volumn 30, Issue 5, 2009, Pages 500-506

  Aminkhani, Ali ^a   Kabiri, Roya ^b   Habibi Khorassani, Sayyed Mostafa ^c   Heydari, Reza ^c   Maghsoodlou, Malek Taher ^c   Marandi, Ghasem ^c   Lashkari, Mojtaba ^c   Rostamizadeh, Mohsen ^c  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b UNIVERSITY OF TABRIZ   (Iran)

^c UNIVERSITY OF SISTAN AND BALUCHESTAN   (Iran)

Author keywords

Acetylenic esters; Diastereoisomers; Karplus equation; Phosphonato esters; Triphenyl phosphite

Indexed keywords

SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL);

2-MERCAPTOBENZOTHIAZOLE; ACETYLENIC ESTER; DIASTEREOISOMERS; DIESTERS; HETEROCYCLIC COMPOUND; KARPLUS EQUATION; PHOSPHONATO ESTER; PYRIDINE-2; THIONES; TRIPHENYL PHOSPHITE;

ESTERS;

EID: 70349587655     PISSN: 17415993     EISSN: 17416000     Source Type: Journal    
DOI: 10.1080/17415990902839450     Document Type: Article

References (39)

1. Bagley, M.C.; Dale, J.W.; Bower, J. Chem. Commun. 2002, 1682-1683
2. Li,Y.X.; Wang, S.H.; Li, Z.M.; Su, N.; Zhao,W.G. Carbohyd. Res. 2006, 341, 2867-2870
3. Tenorio, R.P.; Carvalho, C.S.; Pessanha, C.S.; de Lima, J.G.; de Faria, A.R.; Alves, A.J.; de Melo, E.J.T.; Goes, A. J.S. Bioorg. Med. Chem. Lett. 2005, 15, 2575-2578
4. Kucukguzel, S.G.; Oruc, E.F.; Rollas, S.; Shahin, F.; Ozbek, A. Eur. J. Med. Chem. 2002, 37, 197-206
5. Kato, T.; Ozaki, T.; Tamura, K.; Suzuki,Y.; Akima, M.; Ohi, N. J. Med. Chem. 1999, 442, 3134-3146
6. Dömling, A. Chem. Rev. 2006, 106, 17-89
7. Dömling, A.; Ugi, I. Angew. Chem. Int. Ed. Eng. 2000, 39, 3168-3210
8. Sayed, H.H.; Shamroukh, A.H.; Rashad, A.E. Acta. Pharm. 2006, 56, 1215-1237
9. Bandgar, B.P.; More, P.E.; Kamble, V.T.; Totre, J.V. Arkivoc 2008, xv, 1-8.
10. Engel, R. Chem. Rev. 1977, 77, 349-367
11. Arduago, A.J.; Stewart, C.A. Chem. Rev. 1994, 94, 1215-1237
12. Pietrusiewiewiz, K.M.; Zabloka, M. Chem. Rev. 1994, 94, 1375-1411
13. Bestmann, H.J. Angew. Chem. Int. Ed. 1965, 4, 583-587
14. Bestmann, H.J. Angew. Chem. Int. Ed. 1977, 16, 349-364.
15. Yavari, I.; Alizadeh, A. Tetrahedron 2001, 57, 9873-9875
16. Yavari, I.; Adib, M.; Jahani-Moghaddam, F.; Bijanzadeh, H.R. Tetrahedron 2002, 58, 6901-6906
17. Balaraman, E.; Kumaraswamy, K.C. Synthesis 2004, 3037- 3042
18. (d)Kolodiazhnyi, O.I. Tetrahedron 1996, 52, 1855-1929
19. Barluenga, J.; Lopez, F.; Palacios, F. J. Chem. Soc. Chem. Commun. 1986, 1574-1575
20. Ramazani, A.; Kazemizadeh,A.R.; Ahmadi, E.; Noshiranzadeh, N.; Souldozi, A. Curr. Org. Chem. 2008, 12, 59-82
21. Maghsoodlou, M.T.; Habibi Khorassani, S.M.; Hazeri, N.; Nassiri, M. Phosphorus Sulfur Silicon 2006, 181, 1363-1369
22. Maghsoodlou, M.T.; Hazeri, N.; Habibi-Khorassani, S.M.; Saghatforoush, L.; Rofouei, M.K.; Rezaie, M. Arkivoc 2006, xiii, 117-123
23. Maghsoodlou, M.T.; Habibi- Khorassani, S.M.; Rofouei, M.K.; Adhamdoust, S.R.; Nassiri, M. Arkivoc 2006, xii, 145-151
24. Maghsoodlou, M.T.; Habibi-Khorassani, S.M.; Heydari, R.; Hassankhani, A.; Marandi, G.; Nassiri, M.; Mossadegh, E. Mol. Divers. 2007, 11, 87-91
25. Maghsoodlou, M.T.; Hazeri, N.; Habibi-Khorassani, S.M.; Nassiri, M.; Marandi, G.; Afshari, G.; Niroumand, U. J . Sulfur. Chem. 2005, 26, 261-266
26. Saghatforoush, L.; Maghsoodlou, M.T.; Aminkhani, A.; Marandi, G.; Kabiri, R. J. Sulfur. Chem. 2006, 27, 583-588.
27. Habibi-Khorassani, S.M.; Maghsoodlou M.T.; Ebrahimi A.; Zakarianejad M.; Fattahi, M. J. Solution Chem. 2007, 36, 1117-1127
28. Habibi-Khorassani, S.M.; Maghsoodlou, M.T.; Ebrahimi, A.; Roohi, H.; Zakarianejad, M.; Moradian, M. Prog. React. Kinet. Mech. 2005, 30, 127-143
29. Habibi-Khorassani, S.M.; Maghsoodlou, M.T.; Zakarianejad, M.; Kazemian, M.A.; Nassiri, M.; Karimi, P. Heteroatom. Chem. 2008, 19, 723-732.
30. Breitmaier, E.; Voelter,W. Carbon-13 NMR Spectroscopy, 3rd ed.; VCH Publisher: NewYork, 1990, pp 247-254
31. Mander, L.N. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994
32. Karplus, M. J. Am. Chem. Soc. 1963, 85, 2870-2871
33. Yavari, I.; Anary-Abbasinejad, M.; Hossaini, Z. Org. Biomol. Chem. 2003, 1, 560-564
34. Haasnoot, C.A.G.; De Leeuw, F.A.A.M.; Altona, C. Tetrahedron 1980, 36, 2783-2792.
35. Holmes, R.R. Acc. Chem. Res. 2004, 37, 746-753
36. Maryanoff, B.E.; Reitz, A.B. Chem. Rev. 1989, 89, 863-927.
37. (a)Yavari, I.; Kowsari, E. Dyes Pigments 2008, 77, 103-110
38. Rostami Charati, F.; Maghsoodlou, M.T.; Habibi Khorassani, S.M.; Makha, M. Tetrahedron Lett. 2008, 49, 343-347
39. Maghsoodlou M.T.; Rostami Charati, F.; Habibi Khorassani, S.M.; Ghasemzadeh, M.; Makha, M. Chem. Res. 2008, 55-58.