Synthesis of N-alkoxyindol-2-ones by copper-catalyzed intramolecular N-arylation of hydroxamates

Synlett

Volumn , Issue 17, 2011, Pages 2525-2528

  Kukosha, Tatyana ^a   Trufilkina, Nadezhda ^a   Katkevics, Martins ^a  

^a LATVIAN INSTITUTE OF ORGANIC SYNTHESIS   (Latvia)

Author keywords

arylation; copper; cyclization; hydoxamic acids; lactams

Indexed keywords

1 METHOXY 3,4 DIHYDRO 1H QUINOLIN 2 ONE; COPPER; HYDROXAMIC ACID DERIVATIVE; N ALKOXYINDOL 2 ONE DERIVATIVE; N METHOXYBENZOLACTAM DERIVATIVE; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; CYCLIZATION; PROCESS OPTIMIZATION; REACTION TIME; SYNTHESIS;

EID: 80054085407     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1260328     Document Type: Article

References (44)

1. Henmi T, Sakamoto T, Kikugawa Y, Heterocycles 1997 44 157
2. Kikugawa Y, Shimada M, Matsumoto K, Heterocycles 1994 37 293
3. Pedras M S. C., Chumala P B., Suchy M, Phytochemistry 2003 64 949
4. Kitajima M, Nakamura T, Kogure N, Ogawa M, Mitsuno Y, Ono K, Yano S, Aimi N, Takayama H, [nl]J. Nat. Prod. 2006 69 715
5. Kato H, Yoshida T, Tokue T, Nojiri Y, Hirota H, Ohta T, Williams R M., Tsukamoto S, Angew. Chem. Int. Ed. 2007 46 2254
6. Tsukamoto S, Kato H, Samizo M, Nojiri Y, Onuki H, Hirota H, Ohta T, J. Nat. Prod. 2008 71 2064
7. Bouerat L, Fensholdt J, Liang X, Havez S, Nielsen S F., Hansen J R., Bolvig S, Andersson C, J. Med. Chem. 2005 48 5412, Bouerat L M. E., Fensholdt J, Nielsen S F., Liang X, Havez S E., Andersson E C., Jensen L, Hansen J R., WO 2005058309 2005; Chem. Abstr. 2005, 143, 97259
8. Parkes K E. B., Ermert P, Fässler J, Ives J, Martin J A., Merrett J H., Obrecht D, Williams G, Klumpp K, [nl]J. Med. Chem. 2003 46 1153
9. El-Faham A, Albericio F, Eur. J. Org. Chem. 2009 1499
10. Di Carlo F J., J. Am. Chem. Soc. 1944 66 1420
11. Wright W B. Jr., Collins K H., J. Am. Chem. Soc. 1956 78 221
12. Somei M, Sato H, Kaneko C, Heterocycles 1983 20 1797
13. Kende A S., Thurston J, Synth. Commun. 1990 20 2133
14. Neset S M., Benneche T, Undheim K, Acta Chem. Scand. 1993 47 1141
15. Kikugawa Y, Kawase M, J. Am. Chem. Soc. 1984 106 5728
16. Kawase M, Kitamura T, Kikugawa Y, J. Org. Chem. 1989 54 3394
17. Kikugawa Y, Shimada M, Chem. Lett. 1987 1771
18. For a review, see:, Kikugawa Y, Heterocycles 2009 78 571
19. For reviews on copper-catalyzed cross-couplings, see
20. Ley S V., Thomas A W., Angew. Chem. Int. Ed. 2003 42 5400
21. Beletskaya I P., Cheprakov A V., Coord. Chem. Rev. 2004 248 2337
22. Evano G, Blanchard N, Toumi M, Chem. Rev. 2008 108 3054
23. Schlummer B, Scholz U, Adv. Synth. Catal. 2004 346 1599
24. Surry D S., Buchwald S L., Angew. Chem. Int. Ed. 2008 47 6338
25. Surry D S., Buchwald S L., Chem. Sci. 2011 2 27
26. Wasa M, Yu J.-Q, J. Am. Chem. Soc. 2008 130 14058
27. Jones K L., Porzelle A, Hall A, Woodrow M D., Tomkinson N C. O., Org. Lett. 2008 10 797
28. Porzelle A, Woodrow M D., Tomkinson N C. O., Org. Lett. 2009 11 233
29. Xing X, Wu J, Luo J, Dai W.-M, Synlett 2006 2099
30. van den Hoogenband A, denHartog J A. J., Lange J H. M., Terpstra J W., Tetrahedron Lett. 2004 45 8535
31. Yang B H., Buchwald S L., Org. Lett. 1999 1 35
32. Klapars A, Huang X, Buchwald S L., J. Am. Chem. Soc. 2002 124 7421
33. For reports of the benefit of molecular sieves in the copper-catalyzed cross-coupling reaction, see:, Cristau H.-J, Cellier P P., Spindler J.-F, Taillefer M, Chem. Eur. J. 2004 10 5607
34. Shen Y, Li M, Wang S, Zhan T, Tan Z, Guo C.-C, Chem. Commun. 2009 953
35. Yao B, Zhang Y, Li Y, J. Org. Chem. 2010 75 4554
36. Ma D, Cai Q, Zhang H, Org. Lett. 2003 5 2453
37. Zhang H, Cai Q, Ma D, J. Org. Chem. 2005 70 5164
38. Hosseinzadeh R, Tajbakhsh M, Mohadjerani M, Mehdinejad H, Synlett 2004 1517
39. Altman R A., Buchwald S L., Org.Lett. 2007 9 643
40. de Lange B, Lambers-Verstappen M H., Schmieder-vandeVondervoot L, Sereinig N, de Rijk R, de Vries A H. M., de Vries J G., Synlett 2006 3105
41. Shafir A, Buchwald S L., J. Am. Chem. Soc. 2006 128 8742
42. For recent examples where the hydoxamate N-O moiety serves as an internal oxidant, see:, Guimond N, Gouliaras C, Fagnou K, J. Am. Chem. Soc. 2010 132 6908
43. Patureau F W., Glorius F, Angew. Chem. Int. Ed. 2011 50 1977
44. For a review on oxidative homocoupling reactions, see:, Klussmann M, Sureshkumar D, Synthesis 2011 353