Preparation of novel bicyclic piperazines by reduction of bicyclo[4.2.2]diketopiperazines: rearrangement involving 1,2-bond migration

Tetrahedron Letters

Volumn 48, Issue 38, 2007, Pages 6767-6770

  Du, Yanming ^a   Creighton, Christopher J ^a   Falcone, Brian V ^a   Parker, Michael H ^a   Gauthier, Diane A ^a   Reitz, Allen B ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

1,2 Bond migration; Bicyclic piperazines; LAH reduction; Ring strain; Sigmatropic rearrangement

Indexed keywords

BICYCLO COMPOUND; PIPERAZINE DERIVATIVE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; OLEFINATION; REACTION ANALYSIS; REDUCTION KINETICS; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 34548016335     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.080     Document Type: Article

References (33)

1. Revesz L., Blum E., and Wicki R. Tetrahedron Lett. 46 (2005) 5577-5580
2. Williams R.M., and Cox R.J. Acc. Chem. Res. 36 (2003) 127-139
3. Williams R.M., Cao J., Tsujishima H., and Cox R.J. J. Am. Chem. Soc. 125 (2003) 12172-12178
4. Suwanborirux K., Amnuoypol S., Plubrukarn A., Pummangura S., Kubo A., Tanaka C., and Saito N. J. Nat. Prod. 66 (2003) 1441-1446
5. Scott J.D., and Williams R.M. Chem. Rev. 102 (2002) 1669-1730
6. Toma L., Quadrelli P., Bunnelle W.H., Anderson D.J., Meyer M.D., Cignarella G., Gelain A., and Barlocco D. J. Med. Chem. 45 (2002) 4011-4017
7. Dinsmore C.J., Bergman J.M., Bogusky M.J., Culberson J.C., Hamilton K.A., and Graham S.L. Org. Lett. 3 (2001) 865-868
8. Reitz A.B., and Scott M.K. In: Maryanoff B.E., and Maryanoff C.A. (Eds). Advances in Medicinal Chemistry Vol. 3 (1995), JAI Press, Greenwich, Conn. 1-56
9. Kiely J.S., Hutt M.P., Culbertson T.P., Bucsh R.A., Worth D.F., Lesheski L.E., Gogliotti R.D., Sesnie J.C., Solomon M., and Mich T.F. J. Med. Chem. 34 (1991) 656-663 and references cited therein
10. Trotter, W. B. U.S. Patent 2005/0,227,988 A1, Oct 13, 2005.
11. Muegge I., and Enyedy I. In: Abraham D.J. (Ed). Burger's Medicinal Chemistry & Drug Discovery (2003), Wiley-Interscience, Hoboken, New Jersey 243-280
12. Bicyclic piperazines are used extensively in the fluoroquinolone antibacterials:. Gootz T.D., and Brighty K.E. Med. Res. Rev. 16 (1996) 433-486
13. Du Y., Creighton C.J., Tounge B.A., and Reitz A.B. Org. Lett. 6 (2004) 309-312
14. Diketopiperazines containing the bicyclo[4.2.2]diketopiperazine ring system can also be found in:. Ferioli F., Piccinelli F., Porzi G., and Sandri S. Tetrahedron: Asymmetry 13 (2002) 1181-1187
15. Paradisi F., Porzi G., Rinaldi S., and Sandri S. Tetrahedron: Asymmetry 11 (2000) 4617-4622
16. Williams R.M., Sabol M.R., Kim H.-D., and Kwast A. J. Am. Chem. Soc. 113 (1991) 6621-6633
17. Thomson M.A., and Anderson O.P. Acta Crystallogr., Sect. C C47 (1991) 1984-1986
18. Nakamura D., Kakiuchi K., Koga K., and Shirai R. Tetrahedron Lett. 8 (2006) 6139-6142
19. Weigl M., Bedurftig S., Maier C.A., and Wünsch B. Bioorg. Med. Chem. 10 (2002) 2245-2257
20. Falorni M., Porcheddu A., and Giacomelli G. Tetrahedron: Asymmetry 7 (1996) 1999-2005
21. Creighton C.J., Leo G.C., Du Y., and Reitz A.B. Bioorg. Med. Chem. Lett. 12 (2004) 4375-4385
22. Elguero J., Jacquier R., and Tizané D. Tetrahedron 27 (1971) 133-142
23. Mićović V.M., and Mihailović M.Lj. J. Org. Chem. 18 (1953) 1190-1200
24. Nystrom R.F., and Brown W.G. J. Am. Chem. Soc. 70 (1948) 3738-3740
25. Chen F.-L., and Sung K. Tetrahedron Lett. 47 (2006) 2899-2903
26. Lohray B.B., Bhushan V., Reddy A.S., and Rao V.V. Indian J. Chem., Sect. B 39B (2000) 297-299
27. Ramsden N.G., Fleet G.W.J., and Namgoong S.K. J. Chem. Soc., Perkin Trans. 2 (1991) 1991-1993
28. For examples of reactions promoted by the relief of ring strain see:. Limanto J., Khuong K.S., Houk K.N., and Snapper M.L. J. Am. Chem. Soc. 125 (2003) 16310-16321 and references therein
29. The ring expansion of 7-azabicyclo[2.2.1]hept-2-aminyl radicals may also be promoted in part by the relief of ring strain:. Moreno-Vargas A.J., and Vogel P. Tetrahedron Lett. 44 (2003) 5069-5073
30. Goto M., Akimoto K.-I., Aoki K., Shindo M., and Koga K. Tetrahedron Lett. 40 (1999) 8129-8132
31. Balachander N., Wang S.S., and Sukenik C.N. Tetrahedron Lett. 27 (1986) 849-852
32. Wang S.S., and Sukenik C.N. J. Org. Chem. 50 (1985) 653-656
33. Wang S.S., and Sukenik C.N. J. Org. Chem. 50 (1985) 5448-5450