Iron/palladium-catalyzed intramolecular hydroamination: An expedient synthesis of pyrrole-annulated coumarin and quinolone derivatives

Synthesis

Volumn , Issue 24, 2010, Pages 4207-4212

  Majumdar, K C ^a   De, Nirupam ^a   Roy, B ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

aminoalkynes; FeCl3; hydroamination; pyrrolocoumarin; pyrroloquinolone

Indexed keywords

AMINOALKYNES; FECL3; HYDROAMINATIONS; PYRROLOCOUMARIN; PYRROLOQUINOLONE;

ACETYLENE; CATALYSIS; SYNTHESIS (CHEMICAL);

AMINATION;

COUMARIN DERIVATIVE; FERRIC CHLORIDE; PALLADIUM; PYRROLOCOUMARIN DERIVATIVE; PYRROLOQUINOLONE DERIVATIVE; QUINOLONE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CYCLIZATION; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROAMINATION; MOLECULAR INTERACTION; PROCESS OPTIMIZATION; SOLVENT EFFECT;

EID: 78650174773     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258311     Document Type: Article

References (49)

1. Glasby J S., Encyclopedia of Alkaloids Plenum Press New York 1975
2. Cacchi S, Fabrizi G, Chem. Rev. 2005 105 2873
3. Li J J., Gribble G W., Palladium in Heterocyclic Chemistry Pergamon Oxford 2000 Chap. 3
4. Somei M, Yamada F, Nat. Prod. Rep. 2005 22 73
5. Arcadi A, Bianchi G, Marinelli F, Synthesis 2004 610
6. Zhang Y, Donahue J P., Li C.-J, Org. Lett. 2007 9 627
7. Sakai N, Annaka K, Konakahara T, Tetrahedron Lett. 2006 47 631
8. Namba K, Nakagawa Y, Yamamoto H, Imagawa H, Nishizawa M, Synlett 2008 1719
9. Li X, Chianese A R., Vogel T, Crabtree R H., Org. Lett. 2005 7 5437
10. Hagen S E., Domagala J M., Heifetz C L., Sanchez J P., Solomon M, J. Med. Chem. 1990 33 849
11. Raski S R., Williams R M., Chem. Rev. 1998 98 2723
12. Murakami A, Gao G, Omura M, Yano M, Ito C, Furukawa H, Takahasi D, Koshimizu K, Ohigash H, Biorg. Med. Chem. Lett. 2000 10 59
13. Laborde E, Kiely J S., Culbertson T P., Lesheski L E., J. Med. Chem. 1993 36 1964
14. Dickinson J M., Nat. Prod. Rep. 1993 10 71
15. Piorung M C., Blume F, J. Org. Chem. 1999 64 3642
16. 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
17. Rodighiero P, Chilin A, Pastorini G, Guiotto A, [nl]J. Heterocycl. Chem. 1987 24 1041
18. Guiotto A, Chilin A, Manzini P, DallAcqua F, Bordin F, Rodighiero P, Farmaco 1995 50 479
19. Gia O, Mobilio S, Chilin A, Rodghiero P, Palumbo M, J. Photochem. Photobiol., B. 1988 2 435
20. Quanten E, Adriaens P, Schryver F C., Roelandts R, Degreef H, Photochem. Photobiol. 1986 43 485
21. Kontogiorgis C, Litinas K E., Makri A, Nicolaides D N., Vronteli A, Litina D J. H., Pontiki E, Siohou A, [nl]J. Enzyme Inhib. Med. Chem. 2008 23 43
22. Chen L, Hu T.-S, Yao Z.-J, Eur. J. Org. Chem. 2008 36 6175
23. Chen L, Xu M H., Adv. Synth. Catal. 2009 351 2005
24. Ridley C P., Reddy M V. R., Rocha G, Bushman F D., Faulknera D J., Bioorg. Med. Chem. 2002 10 3285
25. Fan H, Peng J, Hamann M T., Hu J H., Chem. Rev. 2008 108 264
26. Yamaguchi T, Fukuda T, Ishibashi F, Iwao M, Tetrahedron Lett. 2006 47 3755
27. Tardy C, Facompre M, Laine W, Baldeyrou B, Garcia-Gravalos D, Francesch A, Mateo C, Pastor A, Jimenez J A., Manzanares I, Cuevasb C, Bailly C, Bioorg. Med. Chem. 2004 12 1697
28. Jiang W, Alford V C., Qiu Y, Bhattacharjee S, John T M., Johnson D H., Kraft P J., Lundeen S G., Sui Z, Bioorg. Med. Chem. 2004 12 1505
29. Yamashkin S A., Yudin L G., Kost A N., Chem. Heterocycl. Compd. (Engl. Transl.) 1983 19 401
30. Ho T C. T., Jones K, Tetrahedron 1997 53 8287
31. Majumdar K C., Mondal S, De N, Synlett 2008 2851
32. Majumdar K C., Mondal S, De N, Synthesis 2009 2385
33. Majumdar K C., Chattopadhyay B, Samanta S, Synthesis 2009 311
34. Majumdar K C., Chakravorty S, De N, Tetrahedron Lett. 2008 49 3419
35. Majumdar K C., Samanta S, Chattopadhyay B, Tetrahedron Lett. 2008 49 7213
36. Tang Z.-Y, Hu O.-S, Adv. Synth. Catal. 2006 348 846
37. Kaspar L T., Ackermann L, Tetrahedron 2005 61 11311
38. Yasuhara A, Takeda Y, Naoyuki S, Sakamoto T, Chem. Pharm. Bull. 2002 50 235
39. Zhang Y, Donahue J P., Li C.-J, Org. Lett. 2007 9 627
40. Kurisaki T, Naniwa T, Yamamoto H, Imagawa H, Nishizawa M, Tetrahedron Lett. 2007 48 1871
41. Hiroya K, Itoh S, Ozawa M, Kanamori Y, Sakamoto T, Tetrahedron Lett. 2002 43 1277
42. Yin Y, Chai Z, Ma W.-Y, Zhao G, Synthesis 2008 4036
43. Trost B M., McClory A, Angew. Chem. Int. Ed. 2007 46 2074
44. Cariou K, Ronan B, Mignani S, Fensterbank L, Malacria M, Angew. Chem. Int. Ed. 2007 46 1881
45. Koradin C, Dohale W, Rodriguez A L., Schmidt B, Knochel P, Tetrahedron 2003 59 1571
46. Terrasson V, Michaux J, Gaucher A, Wehbe J, Marque S, Prim D, Campagne J.-M, Eur. J. Org. Chem. 2007 35 5332
47. Liang Y, Tang S, Zhang X.-D, Mao L.-Q, Xie Y.-X, Li J.-H, Org. Lett. 2006 8 3017
48. Tang S, Xie Y.-X, Li J.-H, Wang N.-X, Synthesis 2007 1841
49. Baldwin J E., J. Chem. Soc., Chem. Commun. 1976 734