A solid phase traceless synthesis of quinoxalinones

Tetrahedron Letters

Volumn 41, Issue 16, 2000, Pages 2835-2838

  Krchňák, Viktor ^a   Szabo, Lajos ^a   Vágner, Josef ^a  

^a SIDDCO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOXALINE DERIVATIVE;

ALKYLATION; ARTICLE; CYCLIZATION; DERIVATIZATION; DRUG SYNTHESIS; HYDROGEN BOND; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE EXTRACTION;

EID: 0342657817     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00297-5     Document Type: Article

References (10)

1. Smith, J.; Krchňák, V. Tetrahedron Lett. 1999, 40, 7633-7636.
2. (a) Lee, J.; Murray, W. V.; Rivero, R. A. J. Org. Chem. 1997, 62, 3874-3879;
3. (b) Morales, G. A.; Corbett, J. W.; DeGrado, W. F. J. Org. Chem. 1998, 63, 1172-1177;
4. (c) Zaragoza, F.; Stephensen, H. J. Org. Chem. 1999, 64, 2555-2557.
5. Swayze, E. E. Tetrahedron Lett. 1997, 38, 8465-8468 and references cited therein.
6. Kerschen, A.; Kaniszai, A.; Botros, I.; Krchňák, V. J. Comb. Chem. 1999, 1, 480-484.
7. 6) of compound 7a: δ 7.59 (s, 1H), 7.62 (d, 1H), 7.92 (d, 1H), 8.32 (s, 1H); compound 7b: δ 2.65 (s, 3H), 8.16 (s, 1H), 8.39 (s, 1H); compound 7c: δ 4.01 (s, 2H), 6.76 (d, 1H), 7.12 (d, 1H), 7.20 (s, 1H); compound 7d: δ 1.25 (d, 3H), 4.04 (q, 1H), 6.87 (s, 1H), 7.09 (s, 1H); compound 7f: δ 0.78 (d, 3H), 0.95 (d, 3H), 1.22 (d, 3H), 1.24 (d, 3H), 3.65 (m, 1H), 3.88 (m, 1H), 7.38 (s, 1H), 7.60 (s, 1H); compound 7g: δ 2.97 (m, 4H), 3.74 (m, 4H), 7.33 (s, 1H), 7.49 (s, 1H), 8.15 (s, 1H); compound 7h: δ 5.22 (s, 2H), 5.71 (s, 1H), 5.95 (s, 1H), 7.72 (d, 1H), 7.79 (s, 1H), 8.06 (d, 1H), 8.45 (s, 1H); compound 7i: δ 2.21 (s, 3H), 5.47 (s, 2H), 7.11 (d, 2H), 7.15 (d, 2H), 7.65 (d, 1H), 7.70 (s, 1H), 8.04 (d, 1H), 8.46 (s, 1H); compound 7j: δ 3.85 (s, 3H), 5.48 (s, 2H), 6.87 (d, 2H), 7.24 (d, 2H), 7.65 (d, 1H), 7.79 (s, 1H), 8.05 (d, 1H), 8.48 (s, 1H) ppm.
8. Krchňák, V.; Paděra, V. Bioorg. Med. Chem. Lett. 1998, 8, 3261-3264.
9. Analytical gradient HPLC profile was run on a ProC18 4.6×50 mm analytical column (YMC, Wilmington, NC), gradient 0-70% of ACN in 7 min. The purity was estimated based on analytical traces at λ=280 nm.
10. 2 and was also observed e.g., when 2-fluoronitrobenzene, 3-fluoro-4-nitrotoluene, 2,5-difluoronitrobenzene, or 1-bromo-4-fluoro-3-nitrobenzene were used in the second combinatorial step. More acid-stable 4-(4-formylphenoxy)butyryl resin prevented premature loss of the product.