Cycloaddition reactions of 1,3-diazabuta-1,3-dienes with alkynyl ketenes

Tetrahedron

Volumn 65, Issue 24, 2009, Pages 4664-4670

  Abbiati, Giorgio ^a   Contini, Alessandro ^a   Nava, Donatella ^a   Rossi, Elisabetta ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

1,3 Diazabuta 1,3 dienes; 2+2 Cycloaddition; 4+2 Cycloaddition; Alkynyl ketenes; Azetidin 2 ones; Dihydropyrimidinones

Indexed keywords

ALKYNYL GROUP; AZETIDINONE DERIVATIVE; HETEROCYCLIC COMPOUND; KETENE DERIVATIVE; PYRIMIDINONE DERIVATIVE;

ARTICLE; CONJUGATION; CYCLOADDITION; DIASTEREOISOMER; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 65149095003     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.04.041     Document Type: Article

References (72)

1. For some reviews see:
2. Jayakumar S., Ishar M.P.S., and Mahajan M.P. Tetrahedron 58 (2002) 379-471
3. Barluenga J., and Tomas M. Synthesis of Heterocycles from Azadienes. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry (1993), Academic, New York, NY 60-80
4. Boger D.L. Tetrahedron 39 (1983) 2869-2939
5. Morel G., Marchand E., Fouvaud A., and Toupet L. J. Org. Chem. 54 (1989) 1185-1191
6. Burger K., and Penninger S. Synthesis (1978) 526-528
7. Jayakumar S., Ishar M.P.S., and Mahajan M.P. Tetrahedron Lett. 39 (1998) 6557-6560
8. Jayakumar S., and Mahajan M.P. Tetrahedron 58 (2002) 2899-2904
9. Ibnusaud I., Padma Malar E.J., and Sundaram N. Tetrahedron Lett. 31 (1990) 7357-7358
10. Barluenga J., Tomàs M., Ballestreros A., and Lopez L.A. Tetrahedron Lett. 30 (1989) 4573-4576
11. Barluenga J., Tomàs M., Ballestreros A., and Lopez L.A. Heterocycles 37 (1994) 1109-1120
12. Mazumdar S.N., Sharma M., and Mahajan M.P. Tetrahedron Lett. 28 (1987) 2641-2642
13. Friot C., Reliquet A., Reliquet F., and Meslin J.C. Synthesis (2000) 695-703
14. Sain B., Singh S.P., and Sandhu S. Tetrahedron Lett. 38 (1991) 5151-5152
15. Sain B., Singh S.P., and Sandhu S. Tetrahedron 48 (1992) 4567-4578
16. Mazumdar S.N., and Mahajan M.P. Tetrahedron Lett. 31 (1990) 4215-4218
17. Burger K., Partscht H., Huber E., Gieren A., Hubner T., and Kaerlein C.P. Chem. Ztg. 108 (1984) 209-210
18. Burger K., Huber E., Kahl T., Partscht H., and Ganzer M. Synthesis (1988) 44-49
19. Burger K., and Penninger S. Synthesis (1978) 524-526
20. Sharma A.K., Mazumdar S.N., and Mahajan M.P. Tetrahedron Lett. 34 (1993) 7961-7964
21. Sharma A.K., Mazumdar S.N., and Mahajan M.P. J. Chem. Soc., Perkin Trans. 1 (1997) 3065-3070
22. Sharma A.K., Hundal G., Obrai S., and Mahajan M.P. J. Chem. Soc., Perkin Trans. 1 (1999) 615-619
23. Matsuda I., Yamamoto S., and Ishii Y. J. Chem. Soc., Perkin Trans. 1 (1976) 1528-1532
24. Mazumdar S.N., Ibnusaud I., and Mahajan M.P. Tetrahedron Lett. 27 (1986) 5875-5876
25. Luthardt P., and Wu{combining double acute accent}rthwein E.U. Tetrahedron Lett. 29 (1988) 921-924
26. Singh S.P., Mahajan A.R., Prajapati D., and Sandhu J.S. Synthesis (1991) 1026-1028
27. Mazumdar S.N., and Mahajan M.P. Tetrahedron 47 (1991) 1473-1484
28. Mazumdar S.N., Mukherjee S., Sharma A.K., Sengupta D., and Mahajan M.P. Tetrahedron 50 (1994) 7579-7587
29. Dey P.D., Sharma A.K., Rai S.N., and Mahajan M.P. Tetrahedron 51 (1995) 7459-7468
30. Sharma A.K., and Mahajan M.P. Heterocycles 40 (1995) 787-800
31. Sharma A.K., and Mahajan M.P. Tetrahedron 40 (1997) 13841-13854
32. Dey P.D., Sharma A.K., Bharatam P.V., and Mahajan M.P. Tetrahedron 40 (1997) 13829-13840
33. Sharma A.K., Jayakumar S., and Mahajan M.P. Tetrahedron Lett. 39 (1998) 7205-7208
34. Mukherjee S., Mazumdar S.N., Sharma A.K., and Mahajan M.P. Heterocycles 47 (1998) 933-950
35. Landreau C., Deniaud D., Reliquet F., Reliquet A., and Meslin J.C. Heterocycles 53 (2000) 2667-2678
36. Arai S., Sakurai T., Asakura H., Fuma S., Shioiri T., and Aoyama T. Heterocycles 55 (2001) 2283-2288
37. Sharma A.K., Jayakumar S., Hundal M.S., and Mahajan M.P. J. Chem. Soc., Perkin Trans. 1 (2002) 774-784
38. Jayakumar S., Singh P., and Mahajan M.P. Tetrahedron 60 (2004) 4315-4324
39. Rossi E., Stradi R., and Visentin P. Tetrahedron 46 (1990) 3581-3592
40. Rossi E., Calabrese D., and Farma F. Tetrahedron 47 (1991) 5819-5834
41. Rossi E., and Pini E. Tetrahedron 52 (1996) 7939-7946
42. Rossi E., Abbiati G., and Pini E. Tetrahedron 53 (1997) 14107-14114
43. Rossi E., Abbiati G., and Pini E. Tetrahedron 55 (1999) 6961-6970
44. Abbiati G., and Rossi E. Tetrahedron 57 (2001) 7205-7212
45. Abbiati G., Cirrincione de Carvalho A., and Rossi E. Tetrahedron 59 (2003) 7397-7402
46. Moore H.W., Hughes G., Srinivasachar K., Fernandez M., Nguyen N.V., Schoon D., and Tranne A. J. Org. Chem. 50 (1985) 4231-4238
47. Nguyen N.V., and Moore H.W. J. Chem. Soc., Chem. Commun. (1984) 1066-1067
48. Alcaide B., Polanco C., and Sierra M.A. J. Org. Chem. 63 (1998) 6786-6796
49. Rosenblum S.B., Huynh T., Afonso A., and Davis Jr. H.R. Tetrahedron 56 (2000) 5735-5742
50. Hunter D.H., and Sim S.K. Can. J. Chem. 50 (1972) 669-677
51. Karupaiyan K., Srirajan V., Deshmukh A.R.A.S., and Bhawal B.M. Tetrahedron 54 (1998) 4375-4386
52. Luthardt P., Moller M.H., Rodewald U., and Würthwein E.U. Chem. Ber. 122 (1989) 1705
53. Weingarten H., Chupp J.P., and White W.A. J. Org. Chem. 32 (1967) 3246-3249
54. Holland B.C., and Gilman N.W. Synth. Commun. 4 (1974) 203-210
55. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. 50 (1975) 4467-4470
56. For a recent review on Sonogashira reaction see:
57. Chinchilla R., and Nájera C. Chem. Rev. 107 (2007) 874-922
58. Sonogashira K. In: Negishi E., and de Meijere A. (Eds). Handbook of Organopalladium Chemistry for Organic Synthesis (2002), John Wiley and Sons, New York, NY
59. Dener J.M., Hart D.J., and Ramesh S. J. Org. Chem. 53 (1988) 6022-6030
60. Blade R.J., Robinson J.E., Peek R.J., and Weston J.B. Tetrahedron Lett. 28 (1987) 3857-3860
61. Ward R.S. In: Patai S. (Ed). The Chemistry of Ketenes and Allenes and Related Compounds (1980), Wiley, New York NY 231 Part 1
62. Browne M., Burnett D.A., Caplen M.A., Chen L.Y., Clader J.W., Domalsky M., Dugar S., Pushpavanam P., Sher R., Vaccaro W., Viziano M., and Zhao H. Tetrahedron Lett. 36 (1995) 2555-2558
63. The formation of this by-product was widely discussed in our previous paper:. Rossi E., Abbiati G., and Nava D. Heterocycles 51 (1999) 1401-1407
64. Bharatam P.V., Senthil Kumar R., and Mahajan M.P. Org. Lett. 2 (2000) 2725-2728
65. Sordo J.A., Gonzalez J., and Sordo T.L. J. Am. Chem. Soc. 114 (1992) 6249-6251
66. Chemouri H., and Mekelleche S.M. J. Mol. Struct.: THEOCHEM 813 (2007) 67-72
67. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
68. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
69. Rudolf K., Spellmeyer D.C., and Houk K.N. J. Org. Chem. 52 (1987) 3708-3710
70. Lopez R., Sordo T.L., Sordo J.A., and Gonzalez J. J. Org. Chem. 58 (1993) 7036-7037
71. Martin M.M., and Sanders E.B. J. Am. Chem. Soc. 89 (1967) 3777-3782
72. Jacobi P.A., Guo J., Rajeswari S., and Zheng W. J. Org. Chem. 62 (1997) 2907-2916