Poly(ethylene glycol) (PEG) as an efficient and recyclable reaction medium for the synthesis of dibenz[b,f]-1,4-oxazepine

Tetrahedron Letters

Volumn 49, Issue 9, 2008, Pages 1495-1497

  Jorapur, Yogesh R ^a   Rajagopal, Gurusamy ^b   Saikia, Prakash J ^c   Pal, Ravindra R ^d  

^a NARA NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

^b Government Arts College for Men (Autonomous)   (India)

^c Inha University   (South Korea)

^d NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; IONIC LIQUID; MACROGOL; MACROGOL 10000; MACROGOL 200; MACROGOL 20000; MACROGOL 3000; MACROGOL 400; MACROGOL 8000; ORGANIC SOLVENT; OXAZEPINE DERIVATIVE; SOLVENT;

ARTICLE; CATALYST; MOLECULAR WEIGHT; PHASE TRANSITION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

TETRA;

EID: 38649113237     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.115     Document Type: Article

References (28)

1. Lankey R.L., and Anastas P.T. Ind. Eng. Chem. Res. 41 (2002) 4498-4502
2. Anastas P.T., and Warner J.C. Green Chemistry: Theory and Practice (1998), Oxford University Press
3. Tucker J.L. Org. Process Res. Dev. 10 (2006) 315-319
4. US EPA Green Chemistry web site. http://www.epa.gov/opptintr/greenchemistry/ (accessed July 2001).
5. Anastas P.T. ACS Symposium Series 819 (2002), American Chemical Society, Washington, DC p 1
6. Greico P.A. Organic Synthesis in Water (1998), Blackie Academic & Professional, London
7. Li C.-J., and Chan T.-H. Organic Reactions in Aqueous Media (1997), Wiley, New York, NY p 199
8. Leadbeater N.E., and Marco M. Org. Lett. 417 (2002) 2973-2976
9. Kamalakar G., Komura K., and Sugi Y. Ind. Eng. Chem. Res. 45 (2006) 6118-6126
10. Weingaertner H., and Franck E.U. Angew. Chem., Int. Ed. 44 (2005) 2672-2692
11. For recent reviews on ionic liquids, see:. Sheldon R. Chem. Commun. (2001) 2399-2407
12. Zhao H., and Malhotra S.V. Aldrichim. Acta 35 (2002) 75-83
13. Wasserscheid P., and Keim W. Angew. Chem., Int. Ed. 39 (2000) 3772-3789
14. Welton T. Chem. Rev 99 (1999) 2071-2083
15. Jorapur Y.R., and Chi D.Y. Bull. Korean Chem. Soc. 27 (2006) 345-354
16. Kitazume T. ACS Symposium Series 819 (2002), American Chemical Society, Washington, DC pp 50-63
17. Yoshida A., Hao X., and Nishikido J. Green Chem. 5 (2003) 554-557
18. Chen J., Spear S.K., Huddleston J.G., and Rogers R.D. Green Chem. 7 (2005) 64-82
19. Samet A.V., Marshalkin V.N., Kislyi K.A., Chernysheva N.B., Strelenko Y.A., and Semenov V.V. J. Org. Chem. 70 (2005) 9371-9376
20. McKenzie T.C. J. Heterocycl. Chem. 17 (1980) 657-659
21. Wardrop A.W.H., Sainsbury G.L., Harrison J.M., and Inch T.D. J. Chem. Soc., Perkin Trans. 1 12 (1976) 1279-1285
22. Higginbottom R., and Suschitzky H. J. Chem. Soc. (1962) 2367-2370
23. Allaway C.L., Daly M., Nieuwenhuyzen M., and Saunders G.C. J. Fluorine Chem. 115 (2002) 91-99
24. Petrenko N.I., Kozlova M.M., and Gerasimova T.N. J. Fluorine Chem. 36 (1987) 93-98
25. +, 100). Anal. Calcd: C, 79.98; H, 4.65; N, 7.17. Found: C, 79.75; H, 4.58; N, 7.23; Registry No. 257-07-8. Poly(ethylene glycol) recycling procedure: To the recovered crude PEG (≈2.0 mL) was added distilled ethanol (10 mL) and passed through a very short pad of silica gel and activated charcoal. The colorless organic layer was evaporated under reduced pressure. PEG was further dried under high vacuum over night and used for the next run.
26. Wang M.L., and Chang K.R. Can. J. Chem. Eng. 69 (1991) 340-346
27. Wei T.B., Chen J.C., Wang X.C., Zhang Y.M., and Wang L.L. Synth. Commun. 26 (1996) 1447-1454
28. Davidson R.S., Patel A.M., Safdar A., and Thornthwaite D. Tetrahedron Lett. 24 (1983) 5907-5910