A simple, convenient method for the synthesis of maleic anhydrides from α-keto esters and alkanoic acid anhydrides using the TiCl 4/n-Bu3N reagent system

Tetrahedron Letters

Volumn 47, Issue 13, 2006, Pages 2107-2109

  Kishorebabu, Neela ^a   Periasamy, Mariappan ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Keto esters; Alkanoic anhydrides; Maleic anhydrides; Titanium tetrachloride

Indexed keywords

2 OXOACID; ACID ANHYDRIDE; ALKANOIC ACID; MALEIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DIELS ALDER REACTION; DRUG SYNTHESIS; POLYMERIZATION;

BETULACEAE;

EID: 33344477291     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.134     Document Type: Article

References (23)

1. W. Kreiser, L. Janitschke, V.L. Ernest, and W.S. Scheldrick Chem. Ber. 112 1979 397
2. D. Teomim, A. Nyska, and A.J. Domd J. Biomed. Mater. Res. 45 1999 258 267
3. R. Po, L. Fiocca, and L. Abis J. Polym. Sci., Part A: Polym. Chem. 35 1997 3241 3248
4. D.L. Trumbo Polym. Bull. 37 1996 161 167
5. R.M. Slade, and B.P. Branchaud J. Org. Chem. 63 1998 3544 3549
6. E.S. Ratemi, J.M. Dolence, C.D. Poulter, and J.C. Vederas J. Org. Chem. 61 1996 6296 6301
7. R.A. Bit, P.D. Davis, L.H. Elliott, W. Harris, C.H. Hill, E. Keech, H. Kumar, G. Lawton, A. Maw, J.S. Nixon, D.R. Vesey, J. Wadsworth, and S.E. Wilkinson J. Med. Chem. 36 1993 21 29
8. G. Pattenden, M.W. Turvill, and A.P. Chorlton J. Chem. Soc., Perkin Trans. 1 1991 2357 2361
9. H.-L. Weidenmuller, F. Cavagna, H.-W. Fehlhaber, and P. Prave Tetrahedron Lett. 13 1972 3519 3522
10. R.F. Heck J. Am. Chem. Soc. 94 1972 2712 2716
11. D. Zargarian, and H. Alper Organometallics 10 1991 2914 2921
12. J. Li, G. Li, H. Jiang, and M. Chen Tetrahedron Lett. 42 2001 6923 6924
13. Y. Sakurai, S. Sakaguchi, and Y. Ishii Tetrahedron Lett. 40 1999 1701 1704
14. B. Gabriele, G. Salerno, M. Costa, and G.P. Chiusoli Tetrahedron Lett. 40 1999 989 990
15. B. Gabriele, G. Salerno, M. Costa, and G.P. Chiusoli Chem. Commun. 1999 1381 1382
16. B. Gabriele, L. Veltri, G. Salerno, M. Costa, and G.P. Chiusoli Eur. J. Org. Chem. 2003 1722 1728
17. M. Periasamy, C. Rameshkumar, and A. Mukkanti J. Organomet. Chem. 649 2002 209 213 and references cited therein
18. M. Periasamy, and V.D. Rao Tetrahedron: Asymmetry 11 1999 1151 1155
19. M. Periasamy, N. KishoreBabu, and K.N. Jayakumar Tetrahedron Lett. 44 2003 8939 8941
20. M. Periasamy, and S. Suresh Tetrahedron Lett. 45 2004 6291 6293
21. 4. The solvent was evaporated and the residue was chromatographed on a silica gel column. Phenyl maleic anhydride 1a (92% yield) was collected using EtOAc/hexane (4:96) mixture as an eluent.
22. 13C NMR δ ppm: 164.8, 138.1, 131.1, 129.7, 128.9, 127.1.
23. P.V. Raghavan, P. Srinivas, V.V. Rao, P. Manojit, and Y.K. Rao Synlett 2002 947 951