Synthesis of novel substituted naphthoquino[b]-benzo[e][1,4]diazepines via Pictet-Spengler cyclization

Tetrahedron

Volumn 63, Issue 16, 2007, Pages 3389-3394

  Wang, Xiao Lei ^a   Zheng, Xiu Fang ^a   Liu, Ren He ^a   Reiner, John ^a   Chang, Jun Biao ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

Benzodiazepine; Cyclization; Naphthoquinone

Indexed keywords

2,3 DIAMINONAPHTHOQUINONE; 4,5 DIHYDRO 1H 1,4 NAPHTHOQUINO[B]BENZO[E][1,4]DIAZEPINE; ALDEHYDE; BENZODIAZEPINE; DIAZEPINE DERIVATIVE; NAPHTHOQUINO[B]BENZO[E][1,4]DIAZEPINE; NAPHTHOQUINONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; PICTET SPENGLER REACTION; PRIORITY JOURNAL;

HUMAN ECHOVIRUS 1;

EID: 33947153856     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.002     Document Type: Article

References (26)

1. Sternbach L.H. Angew. Chem., Int. Ed. Engl. 10 (1971) 34-43
2. Evans B.E., Rittle K.E., Bock M.G., DiPardo R.M., Freidinger R.M., Whitter W.L., Lundell G.F., Veber D.F., Anderson P.S., Chang R.S., Lotti L.V.J., Cerino D.J., Chen T.B., Kling P.J., Kunkel K.A., Springer J.P., and Hirshfield J. J. Med. Chem. 31 (1988) 2235-2246
3. Evans B., Pipe A., Clark L., and Banks M. Bioorg. Med. Chem. Lett. 11 (2001) 1297-1300
4. Wyatt P.G., Allen M.J., Chilcott J., Hickin G., Miller N.D., and Woollard P.M. Bioorg. Med. Chem. Lett. 11 (2001) 1301-1305
5. Stevens S.Y., Bunin B.A., Plunkett M.J., Swanson P.C., Ellman J.A., and Glick G.D. J. Am. Chem. Soc. 118 (1996) 10650-10651
6. Kuo S.C., Ibuka T., Huang L.J., Lien J.C., Yean S.R., Huang S.C., Lednicer D., Morris-Natschke S., and Lee K.H. J. Med. Chem. 39 (1996) 1447-1451
7. Bozzini S., Pitacco P.G., Pizzioli A., and Russo C. J. Heterocycl. Chem. 33 (1996) 1217-1221
8. Luo Y.L., Chou T.C., and Cheng C.C. J. Heterocycl. Chem. 33 (1996) 113-117
9. Knölker H.J., and Sullivan N.O. Tetrahedron 50 (1994) 10893-10908
10. Ghosh A.K., Bilcer G., and Schiltz G. Synthesis (2001) 2203-2229
11. List B., and Castello C. Synlett (2001) 1687-1689
12. Pickering M.V., Dea P., Streeter D.G., and Witkowski J.T. J. Med. Chem. 20 (1977) 818-821
13. Guay V., and Brassard P. J. Heterocycl. Chem. 24 (1987) 1649-1652
14. Bouaziz Z., Nebois P., and Fillion H. Tetrahedron 51 (1995) 4057-4064
15. For review, see:. Royer J., Bonin M., and Micouin L. Chem. Rev. 104 (2004) 2311-2352
16. Stokker G.E. Tetrahedron Lett. 37 (1996) 5453-5456
17. Welmaker G.S., and Sabalsk J.E. Tetrahedron Lett. 45 (2004) 4851-4854
18. Archer S., Lewis T.R., Unser M.J., Hopper J.O., and Lape H. J. Am. Chem. Soc. 79 (1957) 5783-5785
19. Kundu B., Sawant D., Partani P., and Kesarwani A.P. J. Org. Chem. 70 (2005) 4889-4892
20. Duncton M.A.J., Smith L.M., Burdzovic-Wizeman S., Burns A., Liu H., Mao Y., Wong W.C., and Kiselyov A.S. J. Org. Chem. 70 (2005) 9629-9631
21. Che X., Zheng L.Y., Dang Q., and Bai X. Tetrahedron 62 (2006) 2563-2568
22. Zhang L., Meier W., Wats E., Costello T.D., Ma P., Ensinger C.L., Rodgers J.M., Jacobson I.C., and Rajagopalan P. Tetrahedron Lett. 36 (1995) 8387-8390
23. Mikhalina T.V., Krasheninina V.N., Fokin E.P., and Rubashko S.V. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk 6 (1990) 115-120
24. Rubashko S.V., Mikhalina T.V., and Fokin E.P. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk 6 (1990) 121-127
25. Shishkina R.P., Ektova L.V., Matoshina K.I., and Fokin E.P. Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk 5 (1982) 136-142
26. Wang, X. L.; Zheng, X. F.; Wang, L.; Reiner, J.; Xie, W. L.; Chang, J. B. Synthesis, in press.