Microwave-assisted 1,3-Dipolar Cycloaddition Reactions of Nitrilimines and Nitrile Oxides

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Hafida Kaddar, Jack Hamelin and Hadj Benhaoua


Abstract

The 1,3-dipolar activity of hydrazonoyl chlorides and oxime chlorides over alumina with various alkenes and alkynes under microwave irradiation is studied; a comparative study between dry media conditions and the procedure in homogeneous solution under microwave and classical heating is described.


References

  1. A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet, P. Jacquault and D. Mathé, Synthesis, 1998, 9, 1213 CrossRef; A. Boruah, D. Prajapaty, J. S. Sandhu and A. C. Ghosh, Tetrahedron Lett., 1996, 37, 4203 CrossRef CAS; A. Diaz-Ortiz, E. Diez-Barra, A. de la Hoz, A. Loupy, A. Petit and L. Sanchez, Heterocycles, 1994, 38, 785 CAS; A. Diaz-Ortiz, E. Diez-Barra, A. de la Hoz, A. Moreno, M. J. Gomez-Escalonilla and A. Loupy, Heterocycles, 1996, 43, 1021 CAS.
  2. B. Touaux, B. Klein, F. Texier-Boullet and J. Hamelin, J. Chem. Res. (S), 1994, 116 Search PubMed; B. Touaux, B. Klein, F. Texier-Boullet and J. Hamelin, J. Heteroatom. Chem., 1998, 3, 351 Search PubMed; A. Saoudi, J. Hamelin and H. Benhaoua, Tetrahedron Lett., 1998, 39, 4033 CrossRef CAS; S. Kasmi, J. Hamelin and H. Benhaoua, Tetrahedron Lett., 1998, 39, 8093 CrossRef CAS.
  3. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis, ed B. G. Kurt Torssell, VCH Publishers, Inc.New York, 1988 Search PubMed; M. H. Hassaneen, H. A. Moussa, S. T. Ezmirly and A. S. Shawali, Can. J. Chem., 1988, 66, 1386 Search PubMed.
  4. K. Bougrin, M. Soufiaoui, A. Loupy and P. Jacquault, New. J. Chem., 1995, 19, 213 Search PubMed.
  5. A. K. Bose, B. K. Banik and M. S. Manhas, Tetrahedron Lett., 1995, 32, 213 CrossRef.
  6. Winterfeldt, Chem Ber., 1964, 97, 1952 CAS.
  7. We used a focused microwave oven Synthewave 402® from Prolabo. This oven was fitted with an open reactor vessel and a stirring device. R. Commarmsot, R. Didenot, J. F. Gardais, Rhone-Poulenc/Prolabo (Pat. No. 84/03496. October 27th, 1986). The temperature was measured using an IR captor, Prolabo (Pat. No. 62241D, 14669 FR. December 23rd 1991).
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