Solid supported microwave-assisted Beckmann rearrangement of ketoximes in dry media

Synthetic Communications

Volumn 34, Issue 11, 2004, Pages 2071-2075

  Matloubi Moghaddam, Firouz ^a   Rad, Abbas Ali Rastegar ^a   Zali Boinee, Hassan ^a  

^a SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Beckmann rearrangement; Ketoxime; Microwave irradiation; Solid support; Solvent free

Indexed keywords

ALUMINUM CHLORIDE; KETOXIME; OXIME; SILICA GEL; SOLVENT; UNCLASSIFIED DRUG; ZINC CHLORIDE;

ARTICLE; BECKMANN REARRANGEMENT; IMMOBILIZATION; MICROWAVE IRRADIATION; SOLID;

EID: 2942644417     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120037921     Document Type: Article

References (14)

1. (a) Gawly, R.E. Org. React. 1988, 35, 1 and references therein;
2. (b) Smith, M.B.; March, J. Advanced Organic Chemistry, 5th Ed.; John Wiley & Sons: New York, 2001; 1415 and references therein.
3. Meshram, H.M. Clay catalyzed facile Beckmann rearrangement of ketoximes. Synth. Commun. 1990, 20, 3253.
4. Bosch, A.I.; De la Cruz, P.; Diez-Barra, E.; Loupy, A.; Langa, F. Microwave assisted Beckmann rearrangement of ketoximes in dry media. Synlett. 1995, 12, 1259.
5. 3 impregnated montmorillonite K10. Synth. Commun. 1997, 27, 379.
6. Khadilkar, B.M.; Upadhyaya, D.J. Studies in Beckmann rearrangement of substituted benzophenone and acetophenone oximes. Synth. Commun. 2002, 32, 1867.
7. Touaux, B.; Texier-Boullet, F.; Hamelin, J. Synthesis of oximes, conversion to nitrile oxides and their subsequent 1,3-dipolar cycloaddition reactions under microwave irradiation and solvent-free reaction conditions. Heteroatom. Chem. 1998, 9, 351.
8. Matloubi Moghaddam, F.; Ghffarzadeh, M.; Abdi-Oskui, S.H. Tandem fries reaction-conjugate addition under microwave irradiation in dry media; one-pot synthesis of flavanones. J. Chem. Res. 1999, 9, 575.
9. Matloubi Moghaddam, F.; Dekamin, M.G. Thia-fries rearrangement of aryl sulfonates in dry media under microwave activation. Tetrahedron Lett. 2000, 41, 3479.
10. Furniss, B.S.; Hannaford, A.J.; Rogers, V.; Smith, P.W.G.; Tatchell, A.R. Qualitative organic analysis; physical constant of organic compounds. In Vogel's Textbook of Practical Organic Chemistry, 4th Ed.; Longman: London & New York, 1978; Chapters VII and VIII, 1113, 1194, 1222.
11. (a) Simons, J.H.; Randal, D.; Archer, S. Hydrogen fluoride as a condensing agent. VII. The acylation of aromatic compounds. J. Am. Chem. Soc. 1939, 61, 1795;
12. (b) Lovern, M.L.; Henry, R.H. Synthesis of ketone derivatives of biphenyl by the Friedel-Crafts reaction. J. Am. Chem. Soc. 1941, 63, 1939.
13. Weste, R.C.; Grasselli, J.G. Handbook of Data on Organic Compound, 2nd Ed.; 1989; CRC Press Inc., Boca Raton, Florida, 33431.
14. WWW.aist.go.jp/RIODBS/SDBS/sdbs/owa/sdbs_sea.ere_frame-sea.