Palladium-catalyzed one-pot synthesis of pyrrole-annulated coumarin, quinolone, and 7-aza-indole derivatives

Synlett

Volumn , Issue 16, 2011, Pages 2369-2373

  Majumdar, K C ^a,b   Ganai, Sintu ^a   Chattopadhyay, Buddhadeb ^a   Ray, Krishanu ^a  

^a UNIVERSITY OF KALYANI   (India)

^b TEZPUR UNIVERSITY   (India)

Author keywords

palladium acetate; pyrrolocoumarin; pyrrolopyridine; pyrroloquinolone

Indexed keywords

2 AMINO 3,5 DIBROMOPYRIDINE; 6 AMINO 5 BROMO 1 METHYL QUINOLONE; 6 AMINO 5 BROMOCOUMARIN; 7 AZA INDOLE DERIVATIVE; ACYCLIC KETONE DERIVATIVE; COUMARIN DERIVATIVE; CYCLIC KETONE DERIVATIVE; INDOLE DERIVATIVE; KETONE DERIVATIVE; N,N DIMETHYLFORMAMIDE; PALLADIUM ACETATE; PYRROLE DERIVATIVE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DEBROMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; ONE POT SYNTHESIS;

EID: 80053051451     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1260312     Document Type: Article

References (42)

1. Boyd D R., Sharma N D., Barr S A., Carroll J G., Mackerracher D, Malone J F., J. Chem. Soc., Perkin Trans. 1 2000 3397
2. Bar G, Parsons A F., Thomas C B., Tetrahedron 2001 57 4719
3. Lee Y R., Kim B S., Kweon H I., Tetrahedron 2000 56 3867
4. Pirrung [nl]M C., Blume F, J. Org. Chem. 1999 64 36-42
5. Dickinson J M., Nat. Prod. Rep. 1993 10 71
6. Jiang W, Alford V C., Qiu Y, Bhattacharjee S, John [nl]T M., Johnson D H., Kraft P J., Lundeen S G., Sui Z, Bioorg. Med. Chem. 2004 12 1505
7. Yamashkin S A., Yudin L G., Kost A N., Chem. Heterocycl. Compd. (Engl. Transl.) 1983 19 401
8. Kontogiorgis C, Litinas K E., Makri A, Nicolaides [nl]D N., Vronteli A, Litina D J. H., Pontiki E, Siohou A, J. Enzyme Inhib. Med. Chem. 2008 23 43
9. Rodighiero P, Chilin A, Pastorini G, Guiotto A, [nl] J. Heterocycl. Chem. 1987 24 1041
10. Guiotto A, Chilin A, Manzini P, DallAcqua F, Bordin F, Rodighiero P, Farmaco 1995 50 479
11. Gia O, Mobilio S, Chilin A, Rodghiero P, Palumbo M, J. Photochem. Photobiol., B. 1988 2 435
12. Quanten E, Adriaens P, Schryver F C., Roelandts R, Degreef H, Photochem. Photobiol. 1986 43 485
13. Kontogiorgis C, Litinas K E., Makri A, Nicolaides [nl]D N., Vronteli A, Litina D J. H., Pontiki E, Siohou A, J. Enzyme Inhib. Med. Chem. 2008 23 43
14. Chen L, Hu T.-S, Yao Z.-J, Eur. J. Org. Chem. 2008 6175
15. Chen L, Xu M H., Adv. Synth. Catal. 2009 351 2005
16. Ridley C P., Reddy M V. R., Rocha G, Bushman [nl]F D., Faulknera D J., Bioorg. Med. Chem. 2002 10 3285
17. Fan H, Peng J, Hamann M T., Hu J H., Chem. Rev. 2008 108 264
18. Yamaguchi T, Fukuda T, Ishibashi F, Iwao M, Tetrahedron Lett. 2006 47 3755
19. Tardy C, Facompr M, Laine W, Baldeyrou B, Garca-Gravalos D, Francesch A, Mateo C, Pastor A, Jimnez J A., Manzanares I, Cuevasb C, Bailly C, Bioorg. Med. Chem. 2004 12 1697
20. Hiremath S P., Badiger G R., Jivanagi A S., Purohit [nl]M G., Indian J. Chem. 1992 313 583
21. Kuethe J T., Wong A, Qu C, Smitrovich J, Davies I W., Hughes D L., J. Org. Chem. 2005 70 2555
22. Van Zandt M C., Jones M L., Gunn D E., Geraci L S., Jones J H., Sawicki D R., Sredy J, Jacot J L., Dicioccio A T., Petrova T, Mitschler A, Podjarny A D., J. Med. Chem. 2005 48 3141
23. Faulkner D, J. Nat. Prod. Rep. 1999 16 155
24. Lounasmaa M, Tolvanen A, Nat. Prod. Rep. 2000 17 175
25. Henry J R., Rupert K C., Dodd J H., Turchi I J., Wadsworth S A., Cavender D E., Fahmy B, Olini G C., Davis J E., Pellegrino-Gensey J L., Schafer P H., Siekierka J J., J. Med. Chem. 1998 41 4196
26. Henry [nl]J R., Rupert K C., Dodd J H., Turchi I J., Wadsworth [nl]S A., Cavender D E., Schafer P H., Siekierka J, [nl] J. Bioorg. Med. Chem. Lett. 1998 8 3335
27. Peter A N., Thomas B, Anna K, Tero L, Peter S, [nl]WO 2004016609 2004; Chem. Abstr. 2004, 140, 217627
28. Majumdar K C., Chattopadhyay B, Synthesis 2008 921
29. Majumdar K C., Chattopadhyay B, Samanta S, Synthesis 2008 311
30. Majumdar K C., Chakravorty S, Shyam P K., Taher A, Synthesis 2009 403
31. Majumdar K C., Mondal S, Tetrahedron Lett. 2009 49 2418
32. Chen C.-Y, Lieberman D R., Larsen D R., Verhoeven [nl]T R., Reider P J., J. Org. Chem. 1997 62 2676
33. Rodriguez A L., Koradin C, Dohle W, Knochel P, Angew. Chem. Int. Ed. 2000 39 2488
34. Koradin C, Dohle W, Rodriguez A L., Schmid B, Knochel P, Tetrahedron 2003 59 1571
35. Amjad M, Knight D W., Tetrahedron Lett. 2004 45 539
36. Cacchi S, Fabrizi G, Parisi L M., J. Comb. Chem. 2005 7 510
37. Nazar M, Schneider C, Lindenschmidt A, Will D W., Angew. Chem. Int. Ed. 2004 43 4256
38. Roy P J., Dufresne C, Lachance N, Leclerc J.-P, Boisvert M, Wang Z, Leblanc Y, Synthesis 2005 2751
39. Blache Y, Sinibaldi-Troin M.-E, Hichour M, Benezech V, Chavignon O, Gramain J.-C, Teulade J.-C, Chapat J.-P, Tetrahedron 1999 55 1959
40. Lachance N, April M, Joly M.-A, Synthesis 2005 2571
41. Xu Z, Hu W, Zhang F, Li Q, Lu Z, Zhang L, Jia Y, Synthesis 2008 3981
42. Spergel S H., Danielle R, Okoro D R., Pitts W, J. Org. Chem. 2010 75 5316