The synthesis of 2-oxopiperazines by intramolecular Michael addition on solid support

Tetrahedron Letters

Volumn 37, Issue 35, 1996, Pages 6247-6250

  Goff, Dane A ^a   Zuckermann, Ronald N ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; PIPERAZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; TECHNIQUE;

EID: 0030603029     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01382-2     Document Type: Article

References (12)

1. 1. Goff, D.A., Zuckermann, R.N., J. Org. Chem., 1995, 60, 5748.
2. 2. For recent references to cyclopropyl amino acids see Stammer, C.H., Tetrahedron, 1990, 46, 2231; Burgess, K.; Ho, K.K.; Ke, C.Y., J. Org. Chem., 1993, 58, 3767; Burgess, K.; Ho, K.K., J. Org. Chem., 1992, 57, 5931; Mapelli, C., Turocy, G.; Switzer, F.L., Stammer, C.H., J. Org. Chem., 1989, 54, 145; Williams, R.M.; Fegley, G.J., J. Am. Chem. Soc., 1991, 8796 (1991); Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y., J. Org. Chem., 1991, 56, 4167; Koskinen, A.M.P.; Munoz, L.; J. Org. Chem., 1993, 58, 87
3. 2. For recent references to cyclopropyl amino acids see Stammer, C.H., Tetrahedron, 1990, 46, 2231; Burgess, K.; Ho, K.K.; Ke, C.Y., J. Org. Chem., 1993, 58, 3767; Burgess, K.; Ho, K.K., J. Org. Chem., 1992, 57, 5931; Mapelli, C., Turocy, G.; Switzer, F.L., Stammer, C.H., J. Org. Chem., 1989, 54, 145; Williams, R.M.; Fegley, G.J., J. Am. Chem. Soc., 1991, 8796 (1991); Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y., J. Org. Chem., 1991, 56, 4167; Koskinen, A.M.P.; Munoz, L.; J. Org. Chem., 1993, 58, 87
4. 2. For recent references to cyclopropyl amino acids see Stammer, C.H., Tetrahedron, 1990, 46, 2231; Burgess, K.; Ho, K.K.; Ke, C.Y., J. Org. Chem., 1993, 58, 3767; Burgess, K.; Ho, K.K., J. Org. Chem., 1992, 57, 5931; Mapelli, C., Turocy, G.; Switzer, F.L., Stammer, C.H., J. Org. Chem., 1989, 54, 145; Williams, R.M.; Fegley, G.J., J. Am. Chem. Soc., 1991, 8796 (1991); Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y., J. Org. Chem., 1991, 56, 4167; Koskinen, A.M.P.; Munoz, L.; J. Org. Chem., 1993, 58, 87
5. 2. For recent references to cyclopropyl amino acids see Stammer, C.H., Tetrahedron, 1990, 46, 2231; Burgess, K.; Ho, K.K.; Ke, C.Y., J. Org. Chem., 1993, 58, 3767; Burgess, K.; Ho, K.K., J. Org. Chem., 1992, 57, 5931; Mapelli, C., Turocy, G.; Switzer, F.L., Stammer, C.H., J. Org. Chem., 1989, 54, 145; Williams, R.M.; Fegley, G.J., J. Am. Chem. Soc., 1991, 8796 (1991); Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y., J. Org. Chem., 1991, 56, 4167; Koskinen, A.M.P.; Munoz, L.; J. Org. Chem., 1993, 58, 87
6. 2. For recent references to cyclopropyl amino acids see Stammer, C.H., Tetrahedron, 1990, 46, 2231; Burgess, K.; Ho, K.K.; Ke, C.Y., J. Org. Chem., 1993, 58, 3767; Burgess, K.; Ho, K.K., J. Org. Chem., 1992, 57, 5931; Mapelli, C., Turocy, G.; Switzer, F.L., Stammer, C.H., J. Org. Chem., 1989, 54, 145; Williams, R.M.; Fegley, G.J., J. Am. Chem. Soc., 1991, 8796 (1991); Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y., J. Org. Chem., 1991, 56, 4167; Koskinen, A.M.P.; Munoz, L.; J. Org. Chem., 1993, 58, 87
7. 2. For recent references to cyclopropyl amino acids see Stammer, C.H., Tetrahedron, 1990, 46, 2231; Burgess, K.; Ho, K.K.; Ke, C.Y., J. Org. Chem., 1993, 58, 3767; Burgess, K.; Ho, K.K., J. Org. Chem., 1992, 57, 5931; Mapelli, C., Turocy, G.; Switzer, F.L., Stammer, C.H., J. Org. Chem., 1989, 54, 145; Williams, R.M.; Fegley, G.J., J. Am. Chem. Soc., 1991, 8796 (1991); Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y., J. Org. Chem., 1991, 56, 4167; Koskinen, A.M.P.; Munoz, L.; J. Org. Chem., 1993, 58, 87
8. 2. For recent references to cyclopropyl amino acids see Stammer, C.H., Tetrahedron, 1990, 46, 2231; Burgess, K.; Ho, K.K.; Ke, C.Y., J. Org. Chem., 1993, 58, 3767; Burgess, K.; Ho, K.K., J. Org. Chem., 1992, 57, 5931; Mapelli, C., Turocy, G.; Switzer, F.L., Stammer, C.H., J. Org. Chem., 1989, 54, 145; Williams, R.M.; Fegley, G.J., J. Am. Chem. Soc., 1991, 8796 (1991); Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y., J. Org. Chem., 1991, 56, 4167; Koskinen, A.M.P.; Munoz, L.; J. Org. Chem., 1993, 58, 87
9. 3. Carpino, L.A.; Chao, H.G.; Beyermann, M.; Bienert, M., J. Org. Chem., 1991, 56, 2635; Carpino, L.A.; Sadat-Aalaee, D.; Chao, H.G.; DeSelms, R.H., J. Am. Chem. Soc., 1990, 112, 965. Bertho, J.N.; Loffet, A.; Pinel, C.; Reuther, F.; Sennyey, G., Tetrahedron Lett., 1991, 32, 130.
10. 3. Carpino, L.A.; Chao, H.G.; Beyermann, M.; Bienert, M., J. Org. Chem., 1991, 56, 2635; Carpino, L.A.; Sadat-Aalaee, D.; Chao, H.G.; DeSelms, R.H., J. Am. Chem. Soc., 1990, 112, 965. Bertho, J.N.; Loffet, A.; Pinel, C.; Reuther, F.; Sennyey, G., Tetrahedron Lett., 1991, 32, 130.
11. 3. Carpino, L.A.; Chao, H.G.; Beyermann, M.; Bienert, M., J. Org. Chem., 1991, 56, 2635; Carpino, L.A.; Sadat-Aalaee, D.; Chao, H.G.; DeSelms, R.H., J. Am. Chem. Soc., 1990, 112, 965. Bertho, J.N.; Loffet, A.; Pinel, C.; Reuther, F.; Sennyey, G., Tetrahedron Lett., 1991, 32, 130.
12. 2O, 20 min, RT to give crude 2b. The crude products were characterized by hplc (C-18 RP, Vydac, gradient 0-80% acetonitrile with water containing 0.1% TFA over 40 min., 1.0 mL/ min. flow rate. Detection at 214 nm) and electrospray ms. Proton nmr spectra were obtained for all compounds.