Regioselective cleavage of O-benzyl-N-arylamidoximes: Synthesis of N-aryl amidines and amidoximes

Tetrahedron Letters

Volumn 43, Issue 50, 2002, Pages 9089-9092

  Anbazhagan, Mariappan ^a   Boykin, David W ^a   Stephens, Chad E ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

Author keywords

Amidines; Amidoximes; HBr HOAc; O benzylamidoximes; Pd C EtOH

Indexed keywords

AMIDINE; OXIME; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037049227     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02289-X     Document Type: Article

References (29)

1. Zhu B.-Y., Scarborough R.M. Annu. Rep. Med. Chem. 35:2000;83.
2. Smallheer J.M., Olson R.E., Wexler R.R. Annu. Rep. Med. Chem. 35:2000;103.
3. Fevig J.M., Wexler R.R. Annu. Rep. Med. Chem. 34:1999;81.
4. Liebeschuetz J.W., Jones S.D., Morgan P.J., Murray C.W., Rimmer A.D., Roscoe J.M.E., Waszkowycz B., Welsch P.M., Wylie W.A., Young S.C., Martin H., Mahler J., Brady L., Wilkinson K. J. Med. Chem. 45:2002;1221.
5. Collins J.L., Shearer B.G., Oplinger J.A., Lee S., Garvey E.P., Salter M., Duffy C., Burnette T.C., Furfine E.S. J. Med. Chem. 41:1998;2858.
6. Tidwell, R. R.; Boykin, D. W. Dicationic DNA Minor Groove Binders as Antimicrobial Agents in Small Molecule DNA and RNA Binders: From Synthesis to Nucleic Acid Complexes; Demeunynck, M.; Bailly, C.; Wilson, W. D., Eds.; Wiley-VCH: Hoboken, NJ, 2002.
7. Boykin D.W., Kumar A., Hall J.E., Bender B.C., Tidwell R.R. Bioorg. Med. Chem. Lett. 6:1996;3017.
8. Weller T., Alieg L., Beresini M., Blackburn B., Bunting S., Hadvary P., Muller M.H., Knopp D., Levet-Trafit B., Lipari M.T., Modi N.B., Muller M., Refino C.J., Schmitt M., Schonholzer P., Weiss S., Steiner B. J. Med. Chem. 39:1996;3139.
9. Hall J.E., Kerrigan J.E., Ramachandran K., Bender B.C., Stanko J.P., Jones S.K., Patrick D.A., Tidwell R.R. Antimicrob. Agents Chemother. 42:1998;666.
10. Tucker J.A., Clayton T.L., Chidester C.G., Schulz M.W., Harrington L.E., Conrad S.J., Yagi Y., Oien N.L., Yurek D., Kuo M.-S. Bioorg. Med. Chem. 8:2000;601.
11. (a) Stephens, C. E.; Tanious, F.; Kim, S.; Wilson, D. W.; Schell, W. A.; Perfect, J. R.; Franzblau, S. G.; Boykin D. W. J. Med. Chem. 2001, 44, 1741;
12. (b) Werbovetz, K.; Brendle, J.; Stephens, C. E.; Boykin, D. W. US Patent# 60/246,330, filed 11/7/00.
13. Shearer B.G., Oplinger J.A., Lee S. Tetrahedron Lett. 38:1997;179.
14. Khanna I.K., Yu Y., Huff R.M., Weier R.M., Xu X., Koszyk F.J., Collins P.W., Cogburn J.N., Isakson P.C., Koboldt C.M., Masferrer J.L., Perkins W.E., Seibert K., Veenhuizen A.W., Yuan J., Yang D.-C., Zhang Y.Y. J. Med. Chem. 43:2000;3168.
15. Grundmann C., Frommeld H.-C. J. Org. Chem. 31:1966;157.
16. Grundmann C., Dean J.M. J. Org. Chem. 30:1965;2809.
17. Boyer J.H., Frints P.J.A. J. Org. Chem. 33:1968;4554.
18. Briggs L.S., Cambrie R.C., Dean I.C., Rutledge P.S. Aust. J. Chem. 29:1976;357.
19. Prim D., Campagne J.-M., Joseph D., Andrioletti B. Tetrahedron. 58:2002;2041.
20. Anbazhagan M., Stephens C.E., Boykin D.W. Tetrahedron Lett. 43:2002;4221.
21. Judkins B.D., Allen D.G., Cook T.A., Evans B., Sardharwala T.E. Synth. Commun. 26:1996;4351.
22. +, 64%), 265 (18%), 211.2 (6%), 164.1 (8%), 118.1 (75%), 106.1 (100%), 77.1 (45%).
23. Johnstone R.A.W., Wilby A.H., Entwistle I.D. Chem. Rev. 85:1985;129.
24. For a review of the use of AF in transfer hydrogenations, see: Ram S., Ehrenkaufer R.E. Synthesis. 1998;91.
25. The partial reduction of biphenyl derivatives by transfer hydrogenation has been reported: Andrews, M. J.; Pillai, C. N. Indian J. Chem. 1978, 465. Also see Ref. 16.
26. Brown G.R., Foubister A.J. Synthesis. 1982;1036.
27. 2O: C, 64.61; H, 6.39; N, 10.76. Found: C, 64.78; H, 6.10; N, 10.88.
28. 4) and concentrated. The crude product was passed through a short silica gel column as described in method A to yield 145 mg (69%) of the amidine, which was identical spectroscopically to that obtained by method A.
29. 2O: C, 61.85; H, 5.93; N, 10.03. Found: C, 61.81; H, 6.17; N, 9.75.