Cycloaddition reactions of 2,4-diphenyl-1,3-diazabuta-1,3-dienes with isocyanates and isothiocyanates

Tetrahedron

Volumn 59, Issue 37, 2003, Pages 7397-7402

  Abbiati, Giorgio ^a   De Carvalho, Alessandro Cirrincione ^a   Rossi, Elisabetta ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

1,3 diazabuta 1,3 dienes; Isocyanates; Isothiocyanates; Triazin 2 ones; Triazin 2 thiones; 4+2 cycloaddition

Indexed keywords

ALKENE DERIVATIVE; ISOCYANATE; ISOCYANIC ACID DERIVATIVE; ISOTHIOCYANIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYCLOADDITION; INFRARED RADIATION; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REGULATORY MECHANISM; THIN LAYER CHROMATOGRAPHY;

EID: 0042883905     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01124-4     Document Type: Article

References (52)

1. For some recent reviews see: (a) Jayakumar S., Ishar M.P.S., Mahajan M.P. Tetrahedron. 58:2002;379-471 (b) Barluenga J., Tomas M. Synthesis of Heterocycles from Azadienes. Katritzky A.R. Advances in Heterocyclic Chemistry. 1993;60-80 Academic, New York, (c) Boger D.L. Tetrahedron. 39:1983;2869-2939.
2. For some recent reviews see: (a) Jayakumar S., Ishar M.P.S., Mahajan M.P. Tetrahedron. 58:2002;379-471 (b) Barluenga J., Tomas M. Synthesis of Heterocycles from Azadienes. Katritzky A.R. Advances in Heterocyclic Chemistry. 1993;60-80 Academic, New York, (c) Boger D.L. Tetrahedron. 39:1983;2869-2939.
3. For some recent reviews see: (a) Jayakumar S., Ishar M.P.S., Mahajan M.P. Tetrahedron. 58:2002;379-471 (b) Barluenga J., Tomas M. Synthesis of Heterocycles from Azadienes. Katritzky A.R. Advances in Heterocyclic Chemistry. 1993;60-80 Academic, New York, (c) Boger D.L. Tetrahedron. 39:1983;2869-2939.
4. Morel G., Marchand E., Fouvaud A., Toupet L. J. Org. Chem. 54:1989;1185-1191.
5. Burger K., Penninger S. Synthesis. 1978;526-528.
6. Jayakumar S., Ishar M.P.S., Mahajan M.P. Tetrahedron Lett. 39:1998;6557-6560.
7. Padma Malar E.J., Sundaram N. Tetrahedron Lett. 31:1990;7357-7358.
8. (a) Barluenga J., Tomàs M., Ballestreros A., Lopez L.A. Tetrahedron Lett. 30:1989;4573-4576
9. (b) Barluenga J., Tomàs M., Ballestreros A., Lopez L.A. Heterocycles. 37:1994;1109-1120.
10. (a) Mazumdar S.N., Sharma M., Mahajan M.P. Tetrahedron Lett. 28:1987;2641-2642
11. (b) Friot C., Reliquet A., Reliquet F., Meslin J.C. Synthesis. 2000;695-703.
12. Sain B., Singh S.P., Sandhu S. Tetrahedron Lett. 38:1991;5151-5152.
13. Sain B., Singh S.P., Sandhu S. Tetrahedron. 48:1992;4567-4578.
14. Mazumdar S.N., Mahajan M.P. Tetrahedron Lett. 31:1990;4215-4218.
15. (a) Burger K., Partscht H., Huber E., Gieren A., Hubner T., Kaerlein C.P. Chem. Ztg. 108:1984;209-210
16. (b) Burger K., Huber E., Kahl T., Partscht H., Ganzer M. Synthesis. 1988;44-49
17. (c) Burger K., Penninger S. Synthesis. 1978;524-526.
18. (a) Sharma A.K., Mazumdar S.N., Mahajan M.P. Tetrahedron Lett. 34:1993;7961-7964
19. (b) Sharma A.K., Mazumdar S.N., Mahajan M.P. J. Chem. Soc., Perkin Trans. 1. 1997;3065-3070
20. (c) Sharma A.K., Hundal G., Obrai S., Mahajan M.P. J. Chem. Soc., Perkin Trans. 1. 1999;615-619.
21. (a) Matsuda I., Yamamoto S., Ishii Y. J. Chem. Soc., Perkin Trans. 1. 1976;1528-1532
22. (b) Mazumdar S.N., Ibnusaud I., Mahajan M.P. Tetrahedron Lett. 27:1986;5875-5876
23. (c) Luthardt P., Wurthwein E.U. Tetrahedron Lett. 29:1988;921-924
24. (d) Ibnusaud I., Padma Malar E.J., Sundaram N. Tetrahedron Lett. 31:1990;7357-7358
25. (e) Singh S.P., Mahajan A.R., Prajapati D., Sandhu J.S. Synthesis. 1991;1026-1028
26. (f) Mazumdar S.N., Mahajan M.P. Tetrahedron. 47:1991;1473-1484
27. (g) Mazumdar S.N., Mukherjee S., Sharma A.K., Sengupta D., Mahajan M.P. Tetrahedron. 50:1994;7579-7587
28. (h) Dey P.D., Sharma A.K., Rai S.N., Mahajan M.P. Tetrahedron. 51:1995;7459-7468
29. (i) Sharma A.K., Mahajan M.P. Heterocycles. 40:1995;787-800
30. (j) Sharma A.K., Mahajan M.P. Tetrahedron. 40:1997;13841-13854
31. (k) Dey P.D., Sharma A.K., Bharatam P.V., Mahajan M.P. Tetrahedron. 40:1997;13829-13840
32. (l) Sharma A.K., Jayakumar S., Mahajan M.P. Tetrahedron Lett. 39:1998;7205-7208
33. (m) Mukherjee S., Mazumdar S.N., Sharma A.K., Mahajan M.P. Heterocycles. 47:1998;933-950
34. (n) Landreau C., Deniaud D., Reliquet F., Reliquet A., Meslin J.C. Heterocycles. 53:2000;2667-2678
35. (o) Arai S., Sakurai T., Asakura H., Fuma S., Shioiri T., Aoyama T. Heterocycles. 2283:2001;2288
36. (p) Sharma A.K., Jayakumar S., Hundal M.S., Mahajan M.P. J. Chem. Soc., Perkin Trans. 1. 6:2002;774-784.
37. Rossi E., Abbiati G., Pini E. Tetrahedron. 53:1997;14107-14114.
38. Rossi E., Abbiati G., Pini E. Tetrahedron. 55:1999;6961-9670.
39. Abbiati G., Rossi E. Tetrahedron. 57:2001;7205-7212.
40. For a recent review see: Ozaki S. Chem. Rev. 72:1972;457-496.
41. For a recent review see: Mukerjee A.K., Ashare R. Chem. Rev. 91:1991;1-24.
42. Burger K., Wassmuth U., Forster B., Penninger S. Z. Naturforsch. B Anorg. Chem. Org. Chem. 39:1984;1442-1452.
43. (a) Barluenga J., Tomas M., Ballesteros A., Lopez L.A. Synthesis. 3:1989;228-229
44. (b) Dalla Croce P., Ferraccioli R., La Rosa C. Heterocycles. 45:1997;1309-1318
45. (c) Landreau C., Deniaud D., Reliquet A., Reliquet F., Meslin J.C. J. Heterocycl. Chem. 38:2001;93-98.
46. Bartman W. Chem. Ber. 100:1967;2938-2945.
47. Arnold R.G., Nelson J.A., Verbanc J.J. Chem. Rev. 57:1957;47-76.
48. Abdel-Rahman M.A. Synth. Commun. 23:1993;1427-1436.
49. Rossi E., Celentano G., Stradi R., Strada A. Tetrahedron Lett. 31:1990;903-906
50. (b) Rossi E., Calabrese D., Farma F. Tetrahedron. 47:1991;5819-5834.
51. Tennant G. Barton D., Ollis W.D. Comprensive Organic Chemistry. 1979;513-527 Pergamon, Oxford.
52. Rossi E., Abbiati G., Nava D. Heterocycles. 51:1999;1401-1407.