A novel isoxazole-based scaffold for combinatorial chemistry

Tetrahedron Letters

Volumn 41, Issue 31, 2000, Pages 5971-5974

  Batra, S ^a   Rastogi, S K ^a   Kundu, B ^a   Patra, A ^a   Bhaduri, A P ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

5 isoxazolecarboxaldehyde; Baylis Hillman reaction; Combinatorial chemistry; SPOS; Wittig reaction

Indexed keywords

ALKENE; AMINE; AMINOALCOHOL; IMINE; ISOXAZOLE DERIVATIVE; OXIME;

ARTICLE; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; POLYMERIZATION; SOLID STATE; SYNTHESIS;

EID: 0034729961     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00951-5     Document Type: Article

References (10)

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4. (b) Wang, G. T.; Chen, Y.; Wang, S.; Sciotti, R.; Sowin, T. Tetrahedron Lett. 1997, 38, 1895.
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7. Patra, A.; Batra, S.; Kundu, B.; Joshi, B. S.; Roy, R.; Bhaduri, A. P. Synthesis 2000 (communicated).
8. 2), 5.18 (m, 1H, CH), 5.23 (m, 1H, CH), 6.51 (s, 2H, 2×CH), 6.92 (d, 4H, J=9 Hz, Ar-H), 7.61, 7.64 (d, 4H, J=9 Hz, Ar-H). Wittig reaction: To the resin loaded with aldehyde (50 mg) in THF (400 μL) was added triphenyl phosphonium methyl iodide (5 equivalents) and solution of NaOMe (6 equivalents) in MeOH (100 μL) and the reaction was stirred at 60°C for 6 h. Thereafter the resin was sequentially washed with 50% aq. MeOH (10×4 mL), MeOH and ether (6×4 mL). The resin was cleaved and freeze dried as mentioned above to obtain the product. Nitroaldol condensation reaction: To the resin loaded aldehyde (50 mg) in THF (200 μL) was added nitromethane (30 equivalents), ethanol (30 equivalents) and triethylamine (15 equivalents) and the reaction was shaken at 800 rpm for 3 h. Thereafter the resin was washed with THF, DMF, MeOH, DCM and ether (5×3 mL each). The cleavage of resin and freeze-drying of the residue was performed as mentioned above.
9. Richter, H.; Walk, T.; Holtzel, A.; Jung, G. J. Org. Chem. 1999, 64, 1364.
10. Bheemshanker; Kulkarni, A.; Gawsari, A. J. Comb. Chem. 1999, 1, 373.