Indium(III) chloride-catalyzed conversion of {[(Benzyloxy)carbonyl]amino}- substituted sulfones with 2-[(Trimethylsilyl)oxy]furan: A facile access to γ-butenolactone derivatives containing a protected amino group

Helvetica Chimica Acta

Volumn 94, Issue 6, 2011, Pages 1048-1052

  Das, Biswanath ^a   Sudhakar, Chithaluri ^a   Reddy, Parigi Raghavendar ^a   Kashanna, Jajula ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Butenolactone derivatives; Catalysis; Furan, 2 (trimethylsilyl)oxy ; Indium chloride; Sulfones

Indexed keywords

AMINO GROUP; FACILE ACCESS; HIGH YIELD; INDIUM CHLORIDE; ROOM TEMPERATURE; SULFONES; TRIMETHYLSILYL;

CARBONYLATION; CATALYSIS; CHLORINE COMPOUNDS; INDIUM; ORGANIC POLLUTANTS;

AROMATIC COMPOUNDS;

2 [(TRIMETHYLSILYL)OXY]FURAN; FURAN DERIVATIVE; GAMMA BUTENOLACTONE DERIVATIVE; INDIUM CHLORIDE; LACTONE DERIVATIVE; PHENYLMETHYL N [2,5 DIHYDRO 5 OXOFURAN 2 YL] (NAPHTHALEN 2 YL)METHYL]CARBAMIC ACID; PHENYLMETHYL N [2,5 DIHYDRO 5 OXOFURAN 2 YL] (NAPHTHALEN 2 YL)METHYLCARBAMIC ACID; PHENYLMETHYL N [2,5 DIHYDRO 5 OXOFURAN 2 YL] [4 (1 METHYLETHYL)PHENYL]METHYLCARBAMIC ACID; PHENYLMETHYL N [2,5 DIHYDRO 5 OXOFURAN 2 YL](4 METHYLPHENYL)METHYLCARBAMIC ACID; PHENYLMETHYL N [2,5 DIHYDRO 5 OXOFURAN 2 YL](4-METHYLPHENYL)METHYLCARBAMIC ACID; SULFONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

EID: 79959283219     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201000366     Document Type: Article

References (29)

1. J. A. Joule, K. Mills, ' Heterocyclic Chemistry', 4th edn., Blackwell Science Publishing, Oxford, UK, 2000.
2. R. S. Word, in 'Recent Advances in the Chemistry of Lignans', Vol.a 24, Part E, Ed. Atta-ur-Rahman, Elsevier, Amsterdam, 2000, pp.a 739-798.
3. J. R. Hanson, Nat. Prod. Rep. a 2002, 51, 4571.
4. S. Raic-Malic, D. Svedruzic, T. Gazivoda, A. Marunovic, A. Hergold-Brundic, A. Nagl, I. Balzarini, E. Declereq, M. Mintas, J. Med. Chem. 2000, 43, 4806.
5. D. T. A. Yousef, R. K. Yamaki, M. Kelly, P. J. Scheuer, J. Nat. Prod. 2002, 65, 2.
6. C. J. Hernandez-Guerrero, E. Zubia, M. S. Ortega, J. Luiscarballo, Tetrahedron 2006, 62, 5392.
7. S. Raic-Malic, A. Hergold-Brundic, A. Nagl, M. Grdisa, J. Med. Chem. 1999, 42, 2673.
8. D. Alonso, I. Font, R. M. Ortuno, J. d'Angelo, A. Guingant, C. Bois, Tetrahedron 1991, 47, 5895.
9. H. Kikuchi, Y. Tsukitani, I. Shimizu, M. Kobayashi, I. Kitagawa, Chem. Pharm. Bull. 1983, 31, 552.
10. B. Terem, P. J. Scheur, Tetrahedron 1986, 42, 4409.
11. G. R. Flematti, E. L. Ghisalberti, K. W. Dixon, R. D. Trengova, Science (Washington, DC, U.S.) 2004, 305, 977.
12. G. Casiraghi, L. Colomb, G. Rassu, P. Spanu, J. Org. Chem. 1990, 55, 2565.
13. G. Casiraghi, L. Colomb, J. Org. Chem. 1991, 56, 2135.
14. G. Rassu, L. Pinna, N. Culeddu, G. Casiraghi, G. Gasparti Fava, M. Belicchia Ferrari, G. Pelosi, Tetrahedron 1992, 48, 727.
15. J. A. Marshall, E. N. Wallace, P. S. Coan, J. Org. Chem. 1995, 60, 796.
16. E. Nagishi, M. Kotora, Tetrahedron 1997, 53, 6707.
17. J. Christoffers, Synlett 2001, 723.
18. S. F. Martini, Acc. Chem. Res. 2002, 35, 895.
19. R. Horon, C. Jacquet, J. Org. Chem. 2003, 68, 1821.
20. S. Ma, Acc. Chem. Res. 2003, 36, 701.
21. S. Ma, Z. Yu, Chem.-Eur. J. 2004, 10, 2078.
22. T. Akiyama, Y. Honma, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2008, 350, 399.
23. B. Das, K. Damodar, D. Saritha, N. Chowdhury, M. Krishnaiah, Tetrahedron Lett. 2007, 48, 7930.
24. B. Das, K. Damodar, B. Shashia Kanth, Y. Srinivas, I. Kalavathi, Synlett 2008, 3133.
25. B. Das, K. Damodar, N. Bhunia, J. Org. Chem. 2009, 74, 5607.
26. W. H. Pearson, A. C. Lindbeck, J. W. Kampf, J. Am. Chem. Soc. 1933, 115, 2622.
27. T. Mecozzi, M. Petrini, J. Org. Chem. 1999, 64, 8970.
28. M. Petrini, Chem. Rev. 2005, 105, 3949
29. M. Petrini, E. Torregiani, Synthesis 2007, 159.