A novel synthesis of functionalized aldehyde equivalents through addition of carbanions on Δ2-oxazolinium cations

Tetrahedron

Volumn 54, Issue 14, 1998, Pages 3567-3574

  Singh, Kamaljit ^a   Singh, Jasbir ^a   Singh, Harjit ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLIDINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032473839     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00089-1     Document Type: Article

References (25)

1. 1. Preliminary communication: Singh, K.; Singh, J.; Singh H. Ind. J. Chem., 1996, 35B, 9, 881.
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6. (e) Singh, K.; Singh, J.; Singh H. Tetrahedron, 1996, 52 (45), 14273.
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13. 1H NMR spectra do not show any signals corresponding to open chain tautomers.
14. 1H NMR spectrum.
15. 9. Fulop, F.; Lazar, L.; Bernath, G.; Sillanpaa, R.; Pihlaja, K. Tetrahedron, 1993, 49, 2115. The effect of solvent on the ring-chain equilibrium of oxazolidines demonstrates that the more polar solvent favours the more polar open chain tautomer.
16. 10. Huckin, S. N.; Weiler, L. J. Am. Chem. Soc., 1974, 96 (4), 1082.
17. 3.
18. 12. 25°C, 0°C, -10°C, -48°C, -78°C.
19. 13. Jerry March, Advanced Organic Chemistry, Reactions, mechanisms and structure (Third edition), Wiley Eastern Limited, New Delhi, 1987, p 219.
20. 14. (a) Singh, K.; Singh, J.; Singh, H. Tetrahedron, 1996, 52, 14273.
21. (b) Singh, K.; Singh, J.; Singh, H. Tetrahedron, 1997, 54, 935.
22. 15. Brinkmeyer, R. S.; Collington, E. W.; Meyers, A. I. Organic Synthesis, 1974, 54, 42-45.
23. 16 Allen, P. A.; Ginos, J. J. Org. Chem., 1968, 28, 1963.
24. 14b.
25. 1H NMR data depicts the products to be a mixture of two tautomeric isomers. From the multiplicities and the integral ratios, the signals marked asterisk seem to belong to one isomer.