An efficient one-pot synthesis of pyrimido[2,1-b][1,3]oxazine derivatives via the reaction of isocyanides with dialkyl acetylenedicarboxylates in the presence of 5-substituted uracils

Journal of Heterocyclic Chemistry

Volumn 49, Issue 2, 2012, Pages 310-314

  Baharfar, Robabeh ^a   Baghbanian, Seyed Meysam ^a  

^a UNIVERSITY OF MAZANDARAN   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

DICARBOXYLIC ACID DERIVATIVE; ISOCYANIC ACID DERIVATIVE; OXAZINE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRIMIDO[2,1 B][1,3]OXAZINE DERIVATIVE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS;

EID: 84860613918     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.863     Document Type: Article

References (25)

1. (a), Zhu, J.; Bienaymé, H., Eds. Multicomponent Reactions; Wiley-VCH: Weinheim, 2005
2. (b), Dömling, A.; Ugi, I., Angew Chem Int Ed 2000, 39, 3169
3. (c), Simon, C.; Constantieux, T.; Rodriguez, J., Eur J Org Chem 2004, 24, 4957
4. (d), Cui, S. L.; Lin, X. F.; Wang, Y. G., J Org Chem 2005, 70, 2866.
5. (a), Winterfeldt, E.; Schumann, D.; Dillinger, H. J., Chem Ber 1969, 102, 1656
6. (b), Dillinger, H. J.; Fengler, G.; Schumann, D.; Winterfeldt, E., Tetrahedron 1974, 30, 2553
7. (c), Junjappa, H.; Saxena, M. K.; Ramaiah, D.; Lohray, B. B.; Rath, N. P.; George, M. V., J Org Chem 1998, 63, 9801
8. (d), Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L., Acc Chem Res 2003, 36, 899.
9. Yavari, I.; Nasiri, F.; Moradi, L.; Djahaniani, H., Tetrahedron Lett 2004, 45, 7099.
10. (a), Yavari, I.; Alizadeh, A.; Anary-Abbasinejad, M.; Bijanzadeh, H. R., Tetrahedron 2003, 59, 6083
11. (b), Baharfar, R.; Hossein nia, R.; Baghbanian, S. M., Lett Org Chem 2008, 5, 128.
12. Swinbourne, J. F.; Hunt, H. J.; Klinkert, G., Adv Heterocycl Chem 1987, 23, 103.
13. (a), Haneishi, T.; Okazaki, T.; Hata, T.; Tamura, C.; Nomura, M.; Naito, A.; Seki, I.; Arai, M., J Antibiot 1971, 24, 797
14. (b), Johnson. P. Y.; Silver, R., J Heterocycl Chem 1973, 10, 1029
15. (c), Mosher, H. S.; Frankel, M. B.; Gregory, M., J Am Chem Soc 1953, 75, 5326
16. (d), Khumtaveeporn, K.; Alper, H., J Org Chem 1995, 60, 8142.
17. (a), Sainsbury, M., In Comprehensive Heterocyclic Chemistry;, Boulton, A. J., Mckillop A., Eds.; Pergamon Press: Canada, 1984; Vol. 3, Part 2B, p 995
18. (b), Kato, T.; Katagiri, N.; Yamamoto, Y., Heterocycles 1980, 14, 1333.
19. (a), Baharfar, R.; Vahdat, S. M.; Baghbanian, S. M., Acta Crystallogr Sect E 2008, E64, o1203
20. (b), Baharfar, R.; Asghari, S.; Hamedaninejad, A.; Abbasi, A.; Ostadzadeh, A.; Bijanzadeh, H. R., Lett Org Chem 2007, 4, 429.
21. Jang, Y. H.; Sowers, L. C.; Cagin, T.; Goddard, W. A., J Phys Chem A 2001, 105, 274.
22. (a), Gondela, A.; Walczak, K., Tetrahedron Lett 2006, 47, 4653
23. (b), Soltani Rad, M. N.; Khalafi-Nezhad, A.; Behrouz, S.; Faghihi, M. A.; Zare, A.; Parhami, A., Tetrahedron 2008, 64, 1778.
24. (a), Ugi, I., Isonitrile Chemistry; Academic Press: New York, London, 1971
25. (b), Ugi, I., Angew Chem Int Ed Engl 1982, 21, 810.