Selective syntheses of benzoxazoles and N-(2-hydroxyaryl)pyrrolidin-2-ones from the corresponding cyclopropyl amides with PPh3/CX4

Tetrahedron

Volumn 62, Issue 10, 2006, Pages 2420-2427

  Yang, Yong Hua ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Benzoxazole; Cyclopropane; Cyclopropyl amide; Pyrrolidin 2 one; Ring expanding reaction; Ring opening reaction; Tetrahalomethane; Triphenylphosphine

Indexed keywords

1 (1 BENZYL 2 HYDROXYETHYL)PYRROLIDIN 2 ONE; 1 (2 HYDROXY 5 METHOXYPHENYL)PYRROLIDIN 2 ONE; 1 (2 HYDROXY 5 METHYLPHENYL)PYRROLIDIN 2 ONE; 1 (2 HYDROXYPHENYL)PYRROLIDIN 2 ONE; 1 (5 CHLORO 2 HYDROXYPHENYL)PYRROLIDIN 2 ONE; 1 (5 FLUORO 2 HYDROXYPHENYL)PYRROLIDIN 2 ONE; 2 (3 BROMOPROPYL)BENZOOXAZOLE; 2 (3 CHLOROPROPYL) 5 FLUOROBENZOOXAZOLE; 2 (3 CHLOROPROPYL) 5 METHOXYBENZOOXAZOLE; 2 (3 CHLOROPROPYL) 5 METHYLBENZOOXAZOLE; 2 (3 CHLOROPROPYL)BENZOOXAZOLE; 2 (3 CHLOROPROPYL)NAPHTHO[2,3 D]OXAZOLE; 2 CYCLOPROPYL 5 FLUOROBENZOOXAZOLE; 2 CYCLOPROPYL 5 METHOXYBENZOOXAZOLE; 2 CYCLOPROPYL 5 METHYLBENZOOXAZOLE; 2 CYCLOPROPYLBENZOOXAZOLE; 2 CYCLOPROPYLNAPHTHO[2,3 D]OXAZOLE; 2 PYRROLIDONE DERIVATIVE; 5 CHLORO 2 (3 CHLOROPROPYL)BENZOOXAZOLE; 5 CHLORO 2 CYCLOPROPYLBENZOOXAZOLE; ACETONITRILE; BENZOXAZOLE DERIVATIVE; CYCLOPROPANE DERIVATIVE; SOLVENT; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HIGH TEMPERATURE; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SOLVENT EFFECT; TEMPERATURE DEPENDENCE;

EID: 32444448205     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.077     Document Type: Article

References (30)

1. R. Appel Angew. Chem., Int. Ed. Engl. 14 1975 801 811
2. R. Rabinowitz, and R. Marcus J. Am. Chem. Soc. 84 1962 1312 1313
3. F. Ramirez, N.B. Desai, and N. Mckelvie J. Am. Chem. Soc. 84 1962 1745 1747
4. L.F. Fieser, and M. Fieser Reagents for Organic Synthesis Vol. 3 1972 Wiley-Interscience New York p 320
5. J.I.G. Gadogan, and R.K. Mackie Chem. Soc. Rev. 3 1974 87 137
6. I. Tömösközi, L. Gruber, and L. Radics Tetrahedron Lett. 16 1975 2473 2476
7. R. Aneja, A.P. Davies, and J.A. Knaggs Tetrahedron Lett. 15 1974 67 70
8. A.W. Friederang, and D.S. Tarbell J. Org. Chem. 33 1968 3797 3800
9. B. Castrol, Y. Chapleur, B. Gross, and C. Selve Tetrahedron Lett. 13 1972 5001 5004
10. I.M. Downie, J.B. Lee, and M.F.S. Matough J. Chem. Soc., Chem. Commun. 1968 1350 1351
11. R. Boigegrain, B. Castrol, and C. Selve Tetrahedron Lett. 16 1975 2529 2530
12. R. Appel, K. Warning, and K.-D. Ziehn Justus Liebigs Ann. Chem. 1975 406 409
13. K. Tamura, H. Mizukami, K. Maeda, H. Watanabe, and K. Uneyama J. Org. Chem. 58 1993 32 35
14. Y.-H. Yang, and M. Shi J. Org. Chem. 70 2005 8645 8648
15. M.J. Milewska, T. Bytner, and T. Połoński Synthesis 1996 1485 1488
16. G.B. Neurath J.W. Gorrod Nicotine Related Alkaloids 1993 Chapman London 61
17. G.R. Cook, L.G. Beholz, and J.R. Stille J. Org. Chem. 59 1994 3575 3584
18. H.-P. Zhang, H. Shigemori, M. Ishibashi, T. Kosaka, G.R. Pettit, Y. Kamano, and J. Kobayashi Tetrahedron 50 1994 10201 10206
19. P.W. Baures, D.S. Eggleston, K.F. Erhard, L.B. Cieslinski, T.J. Torphy, and S.B. Christensen J. Med. Chem. 36 1993 3274 3277
20. C.M. Marson, U. Grabowska, T. Walsgrove, D.S. Eggleston, and P.W. Baures J. Org. Chem. 59 1994 284 290
21. For some of the most recent excellent results in this area, see: (a) S. Ma, and Q. He Angew. Chem., Int. Ed. 43 2004 988 990
22. J. Barluenga, J. Alonso, and F.J. Fañanás J. Am. Chem. Soc. 125 2003 2610 2616
23. M.P. Doyle, M. Yan, W. Hu, and L.S. Gronenberg J. Am. Chem. Soc. 125 2003 4692 4693
24. S.E. Denmark, and W. Pan Org. Lett. 5 2003 1119 1122
25. S. Ma, and G. Wang Angew. Chem., Int. Ed. 42 2003 4215 4217
26. 000=472; R1=0.0511, wR2=0.1176. Diffractometer: Rigaku AFC7R.
27. M. Wada, S. Higashizaki, and A. Tsuboi J. Chem. Res. Miniprint 1985 467 490
28. H.H. Wasserman, and F.J. Vinick J. Org. Chem. 38 1973 2407 2408
29. A. de Raadt, H. Griengl, M. Petsch, P. Plachota, N. Schoo, G. Braunegg, H. Weber, I. Kopper, M. Kreiner, and A. Zeiser Tetrahedron: Asymmetry 7 1996 473 490
30. V.W. Reppe Justus Liebigs Ann. Chem. 596 1955 206