'Michael-Michael-Wittig' reactions of (2,4-dioxobutylidene)phosphoranes with 3-formylchromones

Synlett

Volumn , Issue 3, 2003, Pages 402-404

  Langer, Peter ^a   Holtz, Edith ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

(2,4 dioxobutylidene)triphenylphosphoranes; 4 (2 hydroxybenzoyl)salicylic amides; 4 (2 hydroxybenzoyl)salicylic esters; Michael Michael Wittig reaction

Indexed keywords

AMIDE; CHROMONE DERIVATIVE; PHOSPHORANE DERIVATIVE; SALICYLIC ACID DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; MICHAEL ADDITION; STEREOCHEMISTRY; WITTIG REACTION;

EID: 0037289456     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37104     Document Type: Article

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21. 2NOH-HCl: Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (i) With o-phenylenediamine: Ghosh, C. K.; Khan, S. Synthesis 1980, 701. (j) For conversions into pyrroles and thiophenes: Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133. (k) For a review on 3-formylchromones, see: Ellis, G. P. Heterocyclic Compounds, Vol. 35; Weisberger, A., Ed.; Wiley-Interscience: New York, 1977, 921.
22. 2NOH-HCl: Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (i) With o-phenylenediamine: Ghosh, C. K.; Khan, S. Synthesis 1980, 701. (j) For conversions into pyrroles and thiophenes: Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133. (k) For a review on 3-formylchromones, see: Ellis, G. P. Heterocyclic Compounds, Vol. 35; Weisberger, A., Ed.; Wiley-Interscience: New York, 1977, 921.
23. 2NOH-HCl: Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (i) With o-phenylenediamine: Ghosh, C. K.; Khan, S. Synthesis 1980, 701. (j) For conversions into pyrroles and thiophenes: Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133. (k) For a review on 3-formylchromones, see: Ellis, G. P. Heterocyclic Compounds, Vol. 35; Weisberger, A., Ed.; Wiley-Interscience: New York, 1977, 921.
24. 2NOH-HCl: Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (i) With o-phenylenediamine: Ghosh, C. K.; Khan, S. Synthesis 1980, 701. (j) For conversions into pyrroles and thiophenes: Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133. (k) For a review on 3-formylchromones, see: Ellis, G. P. Heterocyclic Compounds, Vol. 35; Weisberger, A., Ed.; Wiley-Interscience: New York, 1977, 921.
25. 2NOH-HCl: Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (i) With o-phenylenediamine: Ghosh, C. K.; Khan, S. Synthesis 1980, 701. (j) For conversions into pyrroles and thiophenes: Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133. (k) For a review on 3-formylchromones, see: Ellis, G. P. Heterocyclic Compounds, Vol. 35; Weisberger, A., Ed.; Wiley-Interscience: New York, 1977, 921.
26. 2NOH-HCl: Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (i) With o-phenylenediamine: Ghosh, C. K.; Khan, S. Synthesis 1980, 701. (j) For conversions into pyrroles and thiophenes: Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133. (k) For a review on 3-formylchromones, see: Ellis, G. P. Heterocyclic Compounds, Vol. 35; Weisberger, A., Ed.; Wiley-Interscience: New York, 1977, 921.
27. 2NOH-HCl: Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Zehnder, L. R.; Park, F.; Kim, M.; Tran, T.-T. T. J. Org. Chem. 1999, 64, 8736. (i) With o-phenylenediamine: Ghosh, C. K.; Khan, S. Synthesis 1980, 701. (j) For conversions into pyrroles and thiophenes: Fitton, A. O.; Frost, J. R.; Suschitzky, H.; Hougton, P. G. Synthesis 1977, 133. (k) For a review on 3-formylchromones, see: Ellis, G. P. Heterocyclic Compounds, Vol. 35; Weisberger, A., Ed.; Wiley-Interscience: New York, 1977, 921.
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29. For phosphorane 3b, see: (a) Hatanaka, M.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1995, 3719. (b) Banwell, M. G.; Cameron, J. M. Tetrahedron Lett. 1996, 525. (c) Hatanaka, M.; Ishida, A.; Tanaka, Y.; Ueda, I. Tetrahedron Lett. 1996, 401. (d) Ceccarelli, S.; Piarulli, U.; Gennari, C. Tetrahedron Lett. 1999, 153.
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37. 5: C, 67.31; H, 4.93. Found: C, 66.88; H, 5.18. All compounds gave satisfactory spectroscopic and analytical and/or high resolution mass data.