A convenient preparation of N-alkyl and N-arylamines by smiles rearrangement - Synthesis of analogues of diclofenac

Synthetic Communications

Volumn 33, Issue 15, 2003, Pages 2725-2736

  Wadia, M S ^b   Patil, D V ^a  

^a Cusrow Wadia Institute of Technology   (India)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; AMINE; DICLOFENAC; NITROGEN; OXYGEN;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CYCLIZATION; DRUG SYNTHESIS; ELECTRON; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0042063892     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120021996     Document Type: Article

References (23)

1. (a) Bunnet, J.F.; Zahler, R.E. Chem. Rev. 1951, 49, 362;
2. (b) Truce, W.E.; Kreider, E.M.; Brand, W.W. Org. React. 1970, 18, 99;
3. (c) Stevens, T,S.; Watts, W.E. Glowes, W. Selected Molecular Rearrangements; London, 1973; 119.
4. (a) Gerasimora, T.N.; Kolchina, E.F. Russ. Chem. Reviews 1995, 64, 133;
5. (b) Bonvincino, G.E.; Yogodzinski, L.H.; Hardy, Jr., R.A. J. Org. Chem. 1962, 7, 4272.
6. Bayles, R.; Johnson, M.C.; Maisey, R.F.; Turner, R.W. Synthesis 1977, 31 and 33.
7. Greiner, A. Tet. Lett. 1989, 30, 931.
8. Coutts, I.G.C.; Southcott, M.R. J. Chem. Soc. Perkin Trans. I 1990, 767.
9. Soloveva, A.; Guseva, A.G. J. Org. Chem. USSR 1968, 4, 1905.
10. Borne, R.F.; Foye, W.O.; Lemke, T.L.; Williams, D.A. Principles of Medicinal Chemistry; Waverely, B.I. Pvt. Ltd.: New Delhi, India, 1995; 558.
11. Ingomar, S.; Grafe; Helmut; Kurt, H.; Ahrens. Preparation of diclofenac sodium (derivatives) S. African ZA 8904667, 28 Feb. 1990, Chem. Abst. 1990, 113, 190940.
12. (a) Hill, C.M.; Towns, M.B.; Senter, G. J. Am. Chem. Soc. 1949, 71, 257;
13. (b) Leaper, J.M.F.; Bishop, J.R. Botan. Gaz. 1951, 112, 250; Chem. Abst. 1951, 45, 7055.
14. (b) Leaper, J.M.F.; Bishop, J.R. Botan. Gaz. 1951, 112, 250; Chem. Abst. 1951, 45, 7055.
15. Parkhe, A.B.; Bhoi, A.; Porwal, K.K.; Boparai, K.S. Ind. J. Chem. 1981, 20B, 79.
16. Furniss, B.S.; Hannaford, A.J.; Smith, P.W.G.; Tatchell, A.R. Vogel's Textbook of Practical Organic Chemistry; Longmans 5th Ed.; 1991; 1312, 1346, 1364, 1372.
17. Blahak, J. Liebigs Ann. Chem. 1978, 8, 1353.
18. Chapman, A.W. J. Chem. Soc. 1929, 569.
19. Ullmann, F. Annalen 1907, 355, 336.
20. Emerson, W.S. J. Am. Chem. Soc. 1941, 63, 2023.
21. Shudo, K.; Ohta, T.; Okamoto, T. J. Am. Chem. Soc. 1981, 103, 645.
22. Tamura, Y.; Venishi, J.I.; Maeda, H.-D., Choi; Ishibashi, H. Synthesis 1981, 534.
23. Moser, P.; Sallmann, A.; Wiesenberg, I. J. Med. Chem. 1990, 33, 2358.