Solid phase synthesis of tetrahydropyrazine-2-ones by intramolecular Mitsunobu reactions

Tetrahedron Letters

Volumn 40, Issue 31, 1999, Pages 5651-5654

  Kung, Pei Pei ^a   Swayze, Eric ^a  

^a ISIS PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMINOALCOHOL; PYRAZINE DERIVATIVE; RESIN;

AMINATION; ARTICLE; CROSS LINKING; CYCLIZATION; DERIVATIZATION; DRUG SYNTHESIS; MOLECULAR INTERACTION; SOLID STATE;

EID: 0033618314     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01102-8     Document Type: Article

References (15)

1. Bhatt, U.; Mohamed, N.; Just, G.; Roberts, E. Tetrahedron Lett. 1997, 38, 3679.
2. Goff, D. A.; Zuckermann, R. N. Tetrahedron Lett. 1996, 37, 6247.
3. 13C NMR analysis showed neither aldehyde carbonyl carbon resonance (188.0 ppm) nor the benzyl alcohol carbon resonance (69.0 ppm) of the starting MB-CHO resin.
4. Walter, M. W.; Adlington, R. M.; Baldwin, J. E.; Schofield, C. J. J. Org. Chem. 1998, 63, 5179.
5. 2) δ 162.3, 160.4, 157.4 (imino carbon), 139.4, 129.9, 128.6, 128.3, 126.2, 118.0, 106.2, 98.8, 74.5, 65.9, 39.4.
6. Khan, N. M.; Arumugam, V.; Balasubramanian, S. Tetrahedron Lett. 1996, 37, 4819.
7. Swayze, E. E. Tetrahedron Lett. 1997, 38, 8643 and references cited therein.
8. Meienhofer, J.; Waki, M.; Heimer, E. P.; Lambros, T. J.; Makofske, R.; Chang, C.-D. Int. J. Peptide Protein Res. 1979, 13, 35.
9. 2 (3x5 mL) and MeOH (3x5 mL).
10. 2O in 18 min at 0.4 mL/min.
11. Yields were calculated based on the weight of compounds cleaved from support and based on the loading of the starting resin (0.4 mmol/g).
12. Diarra, M. S.; Lavoie, M. C.; Jacques, M.; Darwish, I.; Dolence, E. K.; Dolence, J. A.; Ghosh, A.; Ghosh, M.; Miller, M. J.; Malouin, F. Antimicrob. Agents Chemother. 1996, 40, 2610.
13. Ghosh, M.; Lambert, L. J.; Huber, P. W.; Miller, M. J. Bioorg. Med. Chem. Lett. 1995, 5, 2337.
14. 3 requires 469.2216).
15. 2O in 18 min at 0.4 mL/min.