A short route to the synthesis of pyrroloacridines via Ullmann-Goldberg condensation

Tetrahedron Letters

Volumn 51, Issue 2, 2010, Pages 422-424

  Meesala, Ramu ^a   Nagarajan, Rajagopal ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

2 HALOBENZOIC ACID; 5 AMINO 2 METHYLINDOLE; ACRIDINE DERIVATIVE; ACRIDONE DERIVATIVE; BENZOIC ACID DERIVATIVE; CUPROUS ION; INDOLE DERIVATIVE; PHOSPHORUS DERIVATIVE; PHOSPHORUS OXYCHLORIDE; PYRROLOACRIDINE; PYRROLOACRIDONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; DRUG DESIGN; DRUG SYNTHESIS; POLYMERIZATION; ULLMANN GOLDBERG CONDENSATION; X RAY CRYSTALLOGRAPHY;

EID: 71049179890     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.044     Document Type: Article

References (29)

1. Inman W.D., O'Neill-Johnson M., and Crews P. J. Am. Chem. Soc. 112 (1990) 1-4
2. Gimenez-Arnau E., Missailidis S., and Stevens M.F.G. Anti-Cancer Drug Res. 13 (1998) 431-451
3. McCarthy P.J., Pitts T.P., Gunawardana G.P., Kelly-Borges M., and Pomponi S.A. J. Nat. Prod. 55 (1992) 1664-1668
4. Shochet N.R., Rudi A., Kashman Y., Hod Y., El-Maghrabi M.R., and Spector I. J. Cell. Physiol. 157 (1993) 481-492
5. Tasdemir D., Marshall K.M., Mangalindan G.C., Concepción G.P., Barrows L.R., Harper M.K., and Ireland C.M. J. Org. Chem. 66 (2001) 3246-3248
6. McDonald L.A., Eldredge G.S., Barrows L.R., and Ireland C.M. J. Med. Chem. 37 (1994) 3819-3827
7. West R.R., Mayne C.L., Ireland C.M., Brinen L.S., and Clardy J. Tetrahedron Lett. 31 (1990) 3271-3274
8. Smith C.J., Venables D.A., Hopmann C., Salomon C.E., Jompa J., Tahir A., Faulkner D.J., and Ireland C.M. J. Nat. Prod. 60 (1997) 1048-1050
9. Ford P.W., and Davidson B.S. J. Nat. Prod. 60 (1997) 1051-1053
10. Thale Z., Johnson T., Tenney K., Wenzel P.J., Lobkovsky E., Clardy J., Media J., Pietraszkiewicz H., Valeriote F.A., and Crews P. J. Org. Chem. 67 (2002) 9384-9391
11. Ralifo P., Sanchez L., Nadine C.G., Karen T., Scott Lokey R., Theodore R.H., Frederick A.V., and Crews P. J. Nat. Prod. 70 (2007) 95-99
12. Munawar M.A., and Groundwater P.W. Bull. Korean Chem. Soc. 20 (1999) 456-458
13. Gellerman G., Rudi A., and Kashman Y. Tetrahedron 50 (1994) 12959-12972
14. Alyab'eva T.M., Khoshtariya T.E., Vasil'ev A.M., Tret'yakova L.G., Efimova T.K., and Suvorov N.N. Khim. Geterotskl. Soedin 8 (1979) 1092-1097
15. Suvorov N.N., Alyab'eva T.M., and Khoshtariya T.E. Khim. Geterotskl. Soedin 9 (1978) 1277
16. Wardani A., and Lhomme J. Tetrahedron Lett. 34 (1993) 6411-6414
17. Ullmann F. Ber. Dtsch. Chem. Ges. 36 (1903) 2382-2384
18. Goldberg I. Ber. Dtsch. Chem. Ges. 39 (1906) 1691-1692
19. Goodbrand H.B., and Hu N.-X. J. Org. Chem. 64 (1999) 670-674
20. Arterburn J.B., Pennala M., and Gonzalez A.M. Tetrahedron Lett. 42 (2001) 1475-1477
21. Lang F., Zewge D., Houpis I.N., and Volante R.P. Tetrahedron Lett. 42 (2001) 3251-3254
22. Lindley J. Tetrahedron 40 (1984) 1433-1456
23. Strieter E.R., Blackmond D.G., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 4120-4121
24. Klapars A., Xiaohua H., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 7421-7428
25. Meesala R., and Nagarajan R. Tetrahedron 65 (2009) 6050-6056
26. Olah G.A., Krishnamurti R., and Prakash G.K.S. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic synthesis Vol. 3 (1991), Pergamon, New York 293-339
27. 2: C, 64.87; H, 4.8; N, 8.9. Found: C, 64.81; H, 4.85; N, 8.98.
28. 2: C, 64.78; H, 3.84; N, 8.89. Found: C, 64.81; H, 3.88; N, 8.93.
29. CCDC number of 5g is 737672.