Three-component condensations of aldehydes with N-methoxycarboxamides

Tetrahedron Letters

Volumn 45, Issue 49, 2004, Pages 9007-9010

  Marson, Charles M ^a   Pucci, Sabrina ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

Acetals; Condensation; Hydroxamic acid derivatives; Multicomponent reaction

Indexed keywords

ACETAL DERIVATIVE; ALDEHYDE; ALDEHYDE DERIVATIVE; AMIDE; ANISOLE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; FILTRATION; MANNICH REACTION; POLYMERIZATION;

EID: 8644282649     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.058     Document Type: Article

References (17)

1. C.M. Marson, U. Grabowska, T. Walsgrove, D.S. Eggleston, and P.W. Baures J. Org. Chem. 56 1991 2603
2. C.M. Marson, U. Grabowska, T. Walsgrove, D.S. Eggleston, and P.W. Baures J. Org. Chem. 59 1994 284
3. C.M. Marson, U. Grabowska, and T. Walsgrove J. Org. Chem. 57 1992 5045
4. C.M. Marson, U. Grabowska, A. Fallah, T. Walsgrove, D.S. Eggleston, and P.W. Baures J. Org. Chem. 59 1994 291
5. H.E. Zaugg Synthesis 1984 85
6. H.E. Zaugg Synthesis 1984 181
7. H.E. Zaugg, and W.B. Martin Org. React. 14 1965 52
8. F.F. Blicke Org. React. 1 1942 303
9. J.H. Brewster, and E.L. Eliel Org. React. 7 1953 99
10. C.M. Marson, and A. Fallah J. Chem. Soc., Chem. Commun. 23 1988 83
11. M. Whittaker, C.D. Floyd, P. Brown, and A.J.H. Gearing Chem. Rev. 99 1999 2735
12. P.A. Marks, R.A. Rifkind, V.M. Richon, R. Breslow, T. Miller, and W.K. Kelly Nat. Rev. Cancer 1 2001 194
13. I.A. Motorina, L.A. Sviridova, G.A. Golubeva, and Yu.G. Bundel Tetrahedron Lett. 30 1989 117
14. D.B. Reisner, B.J. Ludwig, F.J. Stiefel, S. Gister, M. Meyer, L.S. Powell, and R.D. Sofia Arzneim.-Forsch. 27 1977 760
15. R.E. Harmon, V.L. Rizzo, and S.K. Gupta J. Heterocycl. Chem. 7 1970 439
16. N-Methoxycarboxamides were prepared by stirring a mixture of a carboxylic acid (1 equiv), ethyl chloroformate (1.2 equiv) and N-methylmorpholine (1.3 equiv) in diethyl ether at 0°C for 15 min. Filtration gave a solution that was added to a solution of O-methylhydroxylamine in methanol and the mixture stirred at 20°C, the reaction being usually complete within 1 h. After work-up the material was purified by chromatography on silica using ethyl acetate 60-80°C petroleum ether or ethyl acetate-toluene as eluent. The solution of hydroxylamine in methanol was prepared by adding O-methylhydroxylamine hydrochloride (1.5 equiv) in methanol to a stirred solution of potassium hydroxide (1.5 equiv) in methanol at 0°C, stirring for 15 min and filtration
17. 13C NMR (75 MHz) δ 173.2, 136.3, 121.1, 102.5, 65.3, 56.1, 49.5, 38.6, 25.6, 18.7, 13.5