1,2-Reduction of α,β-unsaturated hydrazones using dimethylamine-borane/p-toluenesulfonic acid: An easy route to allyl hydrazines

Tetrahedron

Volumn 58, Issue 39, 2002, Pages 7925-7932

  Casarini, Maria E ^a   Ghelfi, Franco ^a   Libertini, Emanuela ^a   Pagnoni, Ugo M ^a   Parsons, Andrew F ^b  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Boron and compounds; Hydrazines; Hydrazones; Reduction

Indexed keywords

ALLYL COMPOUND; BORANE DERIVATIVE; DIMETHYLAMINE; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

ACYLATION; ARTICLE; ATMOSPHERE; CONJUGATE; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION;

EID: 0037163336     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00914-6     Document Type: Article

References (56)

1. Giambastiani G., Pacini B., Porcelloni M., Poli G. J. Org. Chem. 63:1998;804-807.
2. Galeazzi R., Mobbili G., Orena M. Attanasi O., Spinelli D., Targets in Heterocycles Systems, Chemistry and Properties. Vol. 1:1997;355-400. SCI.
3. Ghelfi F., Bellesia F., Forti L., Ghirardini G., Grandi R., Libertini E., Montemaggi M.C., Pagnoni U.M., Pinetti A., De Buyck L., Parsons A.F. Tetrahedron. 55:1999;5839-5852.
4. Curran D.P., Tamine J. J. Org. Chem. 56:1991;2746-2750.
5. Naito T., Honda Y., Bhavakul V., Yamaguchi S., Fujiwara A., Miyata O., Ninomiya I. Chem. Pharm. Bull. 45:1997;1932-1939.
6. Webster F.X., Millar J.G., Silverstein R.M. Tetrahedron Lett. 27:1986;4941-4944.
7. Ghelfi F., Parsons A.F. J. Org. Chem. 65:2000;6249-6253.
8. Gatti, L. N-ammino-2-pirrolidinoni: Rottura del Legame N-N. Thesis, University of Modena e Reggio, 2001.
9. Konig K.H., Zeeh B. Chem. Ber. 103:1970;2052-2061.
10. Tiecco M., Testaferri L., Marini F. Tetrahedron. 52:1996;11841-11848.
11. Hart T.W., Vacher B. Tetrahedron Lett. 33:1992;7215-7218.
12. Feid-Allah H.M. Pharmazie. 36:1981;754-756.
13. Barluenga J., Tomas M. Adv. Heterocycl. Chem. 57:1993;1-80.
14. Buonora P., Olsen J.-P., Oh T. Tetrahedron. 57:2001;6099-6138.
15. Behforouz M., Ahmadian M. Tetrahedron. 56:2000;5259-5288.
16. Boger D.L. Paquette L.A., Heterodiene Additions. Comprehensive Organic Synthesis. Vol. 5:1991;451-512 Pergamon, New York.
17. Jayakumar S., Ishar M.P.S., Mahajan M.P. Tetrahedron. 58:2002;379-471.
18. Palacios F., Aparicio D., de los Santos J.M. Tetrahedron. 50:1994;12727-12742.
19. Cristau H.-J., Gasc M.-B. Tetrahedron Lett. 31:1990;341-344.
20. Attanasi O.A., De Crescentini L., Filippone P., Gatti G., Mantellini F., Santeusanio S. Tetrahedron. 54:1998;7581-7594.
21. Tamion R., Mineur C., Ghosez L. Tetrahedron Lett. 36:1995;8977-8980.
22. Koldobskii A.B., Vakhmistrov V.E., Kalinin V.N. Dokl. Akad. Nauk. 346:1996;771-773. Chem. Abstr. 1996, 125, 166916c.
23. Jolivet S., Toupet L., Texier-Boullet F., Hamelin J. Tetrahedron. 52:1996;5819-5832.
24. Burk M.J., Martinez J.P., Feaster J.E., Cosford N. Tetrahedron. 50:1994;4399-4428.
25. Pérez J.M., Avendaño C., Menéndez J.C. Tetrahedron. 51:1995;6573-6586.
26. Beaudegnies R., Ghosez L. Tetrahedron: Asymmetry. 5:1994;557-560.
27. Lassaletta, J. M. Private communication. See also: Fernández, R.; Ferrete, A.; Lassaletta, J. M.; Llera, J. M.; Martin-Zamora, E. Angew. Chem. Int. Ed. 2002, 41, 831-833.
28. Lassaletta, J. M. Private communication. See also: Fernández, R.; Ferrete, A.; Lassaletta, J. M.; Llera, J. M.; Martin-Zamora, E. Angew. Chem. Int. Ed. 2002, 41, 831-833.
29. Eisch J.J., Sanchez R. J. Org. Chem. 51:1986;1848-1852.
30. Möller F. Houben-Weil. Vol. 11/1:1957;Georg Thieme, Stuttgart. pp 285-289.
31. Tamura Y., Tsugoshi T., Nakajima Y., Kita Y. Synthesis. 1984;930-933.
32. Hudrlik P.F., Hudrlik A.M., Yimenu T., Waugh M.A., Nagendrappa G. Tetrahedron. 44:1988;4399-4428.
33. Dumić M., Korunčev D., Kovačević K., Polak L., Kolbah D. Houben-Weil. Vol. E14b:1990;George Thieme, Stuttgart. pp 487-506.
34. Hutchings R.O., Natale N.R. J. Org. Chem. 43:1978;2299-2301.
35. Hutchings R.O., Milewski C.A., Maryanoff B.E. J. Am. Chem. Soc. 95:1972;3662-3668.
36. Smith R.F., Blondell R.D., Abgott R.A., Lipkowitz K.B., Richmond J.A., Fountain K.A. J. Org. Chem. 39:1974;2036-2040.
37. Kikugawa Y., Kawase M. Synth. Commun. 1979;49-52.
38. Lane C.F. Aldrichim. Acta. 6:1973;51-58.
39. Brown H.C., Kanth J.V.B., Dalvi P.V., Zaidlewicz M. J. Org. Chem. 64:1999;6263-6274.
40. Couturier M., Andresen B.M., Tucker J.L., Dubè P., Brenek S.J., Negri J.T. Tetrahedron Lett. 42:2001;2763-2766.
41. Pelter A., Rosser R.M., Mills S. J. Chem. Soc., Perkin Trans. 1. 1984;717-720.
42. Salunkhe A.M., Burkhardt E.R. Tetrahedron Lett. 38:1997;1519-1522.
43. Alexandre F.-R., Pantaleone D.P., Taylor P.P., Fotheringham I.G., Ager D.J., Turner N.J. Tetrahedron Lett. 43:2002;707-710.
44. Schmitt J., Panouse J.J., Hallot A., Pluchet H., Comoy P., Cornu P.-J. Bull. Soc. Chim. Fr. 1963;816-824.
45. Friestad G.K. Tetrahedron. 57:2001;5461-5496.
46. Fernàndez R., Lassaletta J.M. Synlett. 2000;1228-1240.
47. Tennant G. Barton D., Ollis D., Imines, Nitrones, Nitriles and Isocyanides. . Comprehensive Organic Chemistry. Vol. 2:1979;407-418 Pergamon, New York.
48. Billman J.H., McDowell J.W. J. Org. Chem. 26:1961;1437-1440.
49. Nulu J., Nematollahi J. Tetrahedron Lett. 10:1969;1321-1324.
50. Blair J.A., Gardner R.J. J. Chem. Soc. (C). 1970;1714-1717.
51. McMurray J.E. J. Am. Chem. Soc. 90:1968;6821-6825.
52. Funke M.-A., Mayr H. Chem. Eur. J. 3:1997;1214-1222.
53. Oare D.A., Heathcock C.H. Top. Stereochem. 19:1974;232-236.
54. Tomioka K., Shioya Y., Nagaoka Y., Yamada K. J. Org. Chem. 66:2001;7051-7054.
55. For a comprehensive collection of hydrazone C=N reducing procedures, see: Dumić M., Korunčev D., Kovačević K., Polak L., Kolbah D. Houben-Weil. Vol. E14b:1990;George Thieme, Stuttgart. pp 544-547.
56. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry; Longman: Harlow, UK, 1989; p 876.