Sonogashira/N-acyliminium ion aromatic π-cyclisation processes: access to tetra- and pentacyclic lactams

Tetrahedron

Volumn 64, Issue 37, 2008, Pages 8952-8962

  Grigg, Ronald ^a   Sridharan, Visuvanathar ^a   Sykes, David A ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4,6,7,8,13C OCTAHYDRO[1]BENZOFURO[3,2 C]PYRIDO[1,2 A]AZEPINE; 1,2,3,5,6,11C HEXAHYDRO[1]BENZOFURO[2,3 G]INDOLIZINE; 2 IODO N TOSYLANILINE; 2 IODOPHENOL; 8 [(METHYLPHENYL)SULFONYL] 1,2,3,4,6,7,8,12C OCTAHYDROINDOLO[3,2 A]QUINOLIZINE; 9 [(4 METHYLPHENYL)SULFONYL] 1,3,4,6,7,8,9,13C OCTAHYDRO 2H PYRIDO[1',2':1,2]AZEPINO[4,3 B]INDOLE; BENZOFURAN DERIVATIVE; IMINE; INDOLE DERIVATIVE; IODINE DERIVATIVE; LACTAM DERIVATIVE;

ARTICLE; CYCLIZATION; MANNICH REACTION; ORGANIC CHEMISTRY; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; SONOGASHIRA REACTION;

TETRA;

EID: 48049104835     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.044     Document Type: Article

References (33)

1. Grigg R., Inman M., Kilner C., Koppen I., Marchbank J., Selby P., and Sridharan V. Tetrahedron 63 (2006) 6152-6169
2. Grigg R., Gai X., Khamnaen T., Rajviroongit S., Sridharan V., Zhang L., Collard S., and Keep A. Can. J. Chem. 83 (2005) 990-1005
3. Dondas H.A., Fishwick C.W.G., Gai X., Grigg R., Kilner C., Dumrongchai N., Kongkathip B., Polysuk C., and Sridharan V. Angew. Chem., Int. Ed. 44 (2005) 7570-7574
4. Gardiner M., Grigg R., Kordes M., and Sridharan V. Tetrahedron 57 (2001) 7729-7735
5. Gai X., Grigg R., Rajviroongit S., Sridharan V., and Songarsa S. Tetrahedron Lett. (2005) 5899-5902
6. Fishwick C.W.G., Grigg R., Sridharan V., and Virica J. Tetrahedron 59 (2003) 4451-4468
7. Grigg R., Liu A., Shaw D., Suganthan S., Washington M.L., Woodall D.E., and Yoganathan G. Tetrahedron Lett. 41 (2000) 7125-7128
8. Grigg R., Liu A., Shaw D., Suganthan S., Washington M.L., Woodall D.E., and Yoganathan G. Tetrahedron Lett. 41 (2000) 7129-7133
9. Fielding M.R., Grigg R., Sridharan V., Thornon-Pett M., and Urch C.J. Tetrahedron 57 (2001) 7737-7748
10. Bailey P.D., Morgan K.M., Smith D.I., and Vernon J.M. Tetrahedron Lett. 35 (1994) 7115-7118
11. Bailey P.D., Morgan K.M., Smith D.I., and Vernon J.M. Tetrahedron 59 (2003) 3369-3378
12. Bahajaj A.A., Moore M.H., and Vernon J.M. Tetrahedron 60 (2004) 1235-1246
13. Kaluza Z., Mostowicz D., Dolega G., Mroczko K., and Wojcik R. Tetrahedron 62 (2006) 943-953
14. Dake G. Tetrahedron 62 (2006) 3467-3492
15. Pesquet A., Daiech A., and Van H.L. J. Org. Chem. 71 (2006) 5303-5311
16. Liu J., Swidorski J.J., Peters S.D., and Hsung R.P. J. Org. Chem. 70 (2005) 3898-3902
17. Nilson M.G., and Funk R.L. Org. Lett. 8 (2006) 3833-3836
18. Allin S.M., Gaskell S.N., Towler J.M.R., Page P.C.B., Saha B., McKenzie M.J., and Martin W.P. J. Org. Chem. 72 (2007) 8972-8975
19. Sonogashira reaction reviews:
20. Chinchilla R., and Najera C. Chem. Rev. 107 (2007) 874-922
21. Doucet H., and Hierso J.C. Angew. Chem., Int. Ed. 46 (2007) 834-871
22. Hursthouse M.B., Khan A., Marson C.M., and Porter R.A. Tetrahedron Lett. 36 (1995) 5979-5982
23. Gesson J.P., Jacques J.C., and Rambaud D. Bull. Soc. Chim. Fr. 129 (1992) 227-231
24. Griffiths J., and Murphy J.A. Tetrahedron 48 (1992) 5543-5556
25. Iyer S., and Liebeskind L.S. J. Am. Chem. Soc. 109 (1987) 2759-2770
26. Kundu N.G., Pal M., Mahanty J.S., and Dasgupta S.K. J. Chem. Soc., Chem. Commun. (1992) 41-42
27. Arcadi A., Cacchi S., del Rosario M., Fabrizi G., and Marinelli F. J. Org. Chem. 61 (1996) 9280-9288
28. Cacchi S., Fabrizi G., Marinelli F., Moro L., and Pace P. Synlett (1997) 1363-1366
29. Khan M.W., and Kundu N.G. Synlett (1999) 456-458
30. Zhang H.C., Ye H., Moretto A.F., Brumfield K.K., and Maryanoff B.E. Org. Lett. 2 (2000) 89-92
31. Wu T.Y.H., Ding S., Gray N.S., and Schultz P.G. Org. Lett. 3 (2001) 3827-3830
32. Larock R.C. Comprehensive Organic Transformations (1989), VCH, New York, NY
33. Baldwin J.E. J. Chem. Soc., Chem. Commun. (1976) 734-735