A three-component synthesis of benzochromenodiazocines and chromenopyridines

Tetrahedron Letters

Volumn 54, Issue 15, 2013, Pages 1960-1962

  Dolatkhah, Zahra ^a   Nasiri Aghdam, Mahnaz ^a   Bazgir, Ayoob ^a  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

Author keywords

Chromene; Chromenodiazocines; Chromenopyridines; Multi component

Indexed keywords

CHROMENE DERIVATIVE; CHROMENODIAZOCINE; CHROMENOPYRIDINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 84874947636     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.01.122     Document Type: Article

References (21)

1. Plaskon, A. S.; Grygorenko, O. O.; Ryabukhin, S. V. Tetrahedron 2012, 68, 2743.
2. Elinson, M. N.; Dorofeev, A. S.; Feducovich, S. K.; Gorbunov, S. V.; Nasybullin, R. F.; Stepanov, N. O.; Nikishin, G. I. Tetrahedron Lett. 2006, 47, 7629.
3. Sun, W.; Cama, L. J.; Birzin, E. T.; Warrier, S.; Locco, L.; Mosley, R.; Hammond, M. L.; Rohrer, S. P. Bioorg. Med. Chem. Lett. 2006, 16, 1468.
4. Stachulski, A. V.; Berry, N. G.; Lilian Low, A. C.; Moores, S. L.; Row, E.; Warhurst, D. C.; Adagu, I. S.; Rossignol, J.-F. J. Med. Chem. 2006, 49, 1450.
5. Asal, F. T.; Rakesh, T.; Amir, N. S.; Tahmineh, A.; Deendayal, M.; Abbas, S.; Keykavous, P.; Alireza, F. Med. Chem. 2011, 7, 466.
6. Appukkuttan, P.; Dehaen, W.; Van der Eycken, E. Org. Lett. 2005, 7, 2723.
7. Yoshida, H.; Shirakawa, E.; Honda, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2002, 41, 3247.
8. Vedejs, E.; Galante, R. J.; Goekjian, P. G. J. Am. Chem. Soc. 1998, 120, 3613.
9. Kazanietz, M. G.; Caloca, M. J.; Fujii, T.; Eroles, P.; Garcia-Bermejo, M. L.; Reilly, M.; Wang, H. Biochem. Pharmacol. 2000, 60, 1417.
10. Viladomat, F.; Bastida, J. E.; Codina, C.; Campbell, W. E.; Mathee, S. Phytochemistry 1995, 40, 307.
11. Paudler, W. W.; Zeiler, A. G. J. Org. Chem. 1969, 34, 2138.
12. Yet, L. Chem. Rev. 2000, 100, 2963.
13. Appukkuttan, P.; Dehaen, W.; Van der Eycken, E. Chem. Eur. J. 2007, 13, 6452.
14. Kogen, H.; Toda, N.; Tago, K.; Marumoto, S.; Takami, K.; Ori, M.; Yamada, N.; Koyama, K.; Naruto, S.; Abe, K.; Yamazaki, R.; Hara, T.; Aoyagi, A.; Abe, Y.; Kaneko, T. Org. Lett. 2002, 4, 3359.
15. Harnett, J. J.; Auguet, M.; Viossat, I.; Dolo, C.; Bigg, D.; Chabrier, P.-E. Bioorg. Med. Chem. Lett. 2002, 12, 1439.
16. Pillai, A. D.; Rathod, P. D.; Franklin, P. X.; Patel, M.; Nivsarkar, M.; Vasu, K. K.; Padh, H.; Sudarsanam, V. Biochem. Biophys. Res. Commun. 2003, 301, 183.
17. Antonello, A.; Hrelia, P.; Leonardi, A.; Marucci, G.; Rosini, M.; Tarozzi, A.; Tumiatti, V.; Melchiorre, C. J. Med. Chem. 2005, 48, 28.
18. Detsi, A.; Bouloumbasi, D.; Prousis, K. C.; Koufaki, M.; Athanasellis, G.; Melagraki, G.; Afantitis, A.; Igglessi-Markopoulou, O.; Kontogiorgis, C.; Hadjipavlou-Litina, D. J. J. Med. Chem. 2007, 50, 2450.
19. Typical procedure for the preparation of benzochromenodiazocines 4: A mixture of isatoic anhydride (1 mmol) and NH4OAc (1.5 mmol) or an amine (1 mmol) was stirred in refluxing toluene (5 mL) for 1 h.
20. Anderson, D. R.; Hegde, S.; Reinhard, E.; Gomez, L.; Vernier, W. F.; Lee, L.; Liu, S.; Sambandam, A.; Snider, P. A.; Masih, L. Bioorg. Med. Chem. Lett. 2005, 15, 1587.
21. Evdokimov, N. M.; Magedov, I. V.; Kireev, A. S.; Kornienko, A. Org. Lett. 2006, 8, 899.