N-Phenyl-1,2,4-triazoline-3,5-dione (PTAD) as a dienophilic dinitrogen equivalent: A simple synthesis of 3-amino-1,2,4-benzotriazines from arylcarbodiimides

European Journal of Organic Chemistry

Volumn , Issue 4, 2010, Pages 694-704

  Alajarin, Mateo ^a   Bonillo, Baltasar ^a   Marin Luna, Marta ^a   Sanchez Andradal, Pilar ^a   Vidal, Angel ^a  

^a Campus de Espinardo   (Spain)

Author keywords

Cycloaddition; Nitrogen heterocycles; Synthetic methods; Transition states

Indexed keywords

EID: 74949086691     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901103     Document Type: Article

References (85)

1. a) C. J. Moody, Adv. Heterocycl. Chem. 1982, 30, 1-45
2. b) S. Radl, Adv. Heterocycl. Chem. 1996, 67, 119-205.
3. For recent examples of using PTAD as an enophile, see: a) O. Acevedo, M. E. Squillacote, J. Org. Chem. 2008, 73, 912-922;
4. b) A. Basheer, Z. Rappoport, J. Org. Chem. 2008, 73, 184-190;
5. c) G. C. Vougioukalakis, M. M. Roubelakis, M. N. Alberti, M. Orfanopoulos, Chem. Eur. J. 2008, 14, 9697-9705.
6. For recent examples of using PTAD as a dienophile, see: a) S. Kobayashi, T. Furuya, T. Otani, T. Saito, Tetrahedron 2008, 64, 9705-9716;
7. b) H. W Süennemann, M. G. Banwell, A. deMeijere, Chem. Eur. J. 2008, 14, 7236-7249;
8. c) S. Kobayashi, T. Furuya, T. Otani, T. Saito, Tetrahedron Lett. 2008, 49, 4513-4515;
9. d) M. Alajarin, J. Cabrera, A. Pastor, P. Sanchez-Andrada, D. Bautista, J. Org. Chem. 2008, 73, 963-973.
10. For a recent insight on the mechanism of the Diels-Alder reaction between PTAD and dienes, see: N. A. Alberti, M. Orfanopoulos, Org. Lett. 2009, 11, 1659-1662.
11. a) V. M. Kobal, D. T. Gibson, R. E. Davies, A. Garza, J. Am. Chem. Soc. 1973, 95, 4420-4421
12. b) K. L. Hoffman, G. Maas, M. Regitz, J. Org. Chem. 1987, 52, 3851-3857
13. c) R. Askani, J. P. Chesick, Chem. Ber. 1973, 106, 8-19;
14. d) T. Imagawa, N. Sueda, M. Kawanisi, J. Chem. Soc., Chem. Commun, 1972, 388.
15. a) D. H. R. Barton, A. A. L. Gunatilaka, T. Nakanishi, H. Patin, D. A. Widdowson, B. R. Worth, J. Chem. Soc. Perkin Trans. 1 1976, 821-826;
16. b) R. I. Yakhimovich, N. F. Fursaeva, V. E. Pashinnik, Chem. Nat. Prod. 1985, 21, 98-103;
17. c) K. Ochi, I. Matsunaga, H. Nagano, M. Fukushima, M. Shindo, C. Kanedo, M. Ishikawa, H. F. DeLuca, J. Chem. Soc Perkin Trans. 1 1979, 165-169;
18. d) N. Bosworth, A. Emke, J. M. Midgley, C. J. Moore, W. B. Whalley, G. Fergurson, W. C. Marsh, J. Chem. Soc. Perkin Trans. 1 1977, 805-809.
19. a) A. P. Henderson, E. Mutlu, A. Leclercq, C. Bleasdale, W. Clegg, R. A. Henderson, B. T. Golding, Chem. Commun. 2002, 1956-1957
20. b) A. G. Anastassiou, E. Yakali, J. Chem. Soc., Chem. Commun. 1972, 92-93.
21. a) M. Alajarin, B. Bonillo, P. Sanchez-Andrada, A. Vidal, D. Bautista, Org. Lett. 2009, 11, 1365-1368;
22. b) M. Alajarin, A. Vidal, M.-M. Ortin, D. Bautista, Synlett 2004, 991-994;
23. c) M. Alajarin, A. Vidal, M.-M. Ortin, D. Bautista, New J. Chem. 2004, 28, 570-577;
24. d) M. Alajarin, A. Vidal, M.-M. Ortin, Org. Biomol. Chem. 2003, 1, 4282-4292;
25. e) M. Alajarin, A. Vidal, M.-M. Ortin, Tetrahedron Lett. 2003, 44, 3027-3030;
26. f) M. Alajarin, A. Vidal, F. Tovar, Targets Heterocyel. Syst. 2000, 4, 293-326;
27. g) P. Molina, M. Alajarin, A. Vidal, I Feneau-Dupont, J. P. Declercq, J. Org. Chem. 1991, 56, 4008-4016.
28. a) M. Alajarin, B. Bonillo, A. Vidal, D. Bautista, J. Org. Chem. 2008, 73, 291-294;
29. b) M. Alajarin, B. Bonillo, M.-M. Ortin, P. Sanchez-Andrada, A. Vidal, Org. Lett. 2006, 8, 5645-5648;
30. c) P. Molina, M. Alajarin, P. Sanchez-Andrada, J. Elguero, M. L. Jimeno, J. Org. Chem. 1994, 59, 7306-7315;
31. d) P. Molina, M. Alajarin, A. Vidal, J. Elguero, R. M. Claramunt, Tetrahedron 1988, 44, 2249-2259;
32. e) P. Molina, M. Alajarin, J. R. Saez, Synthesis 1984, 983-986.
33. a) N. A. Lisowskaya, M. Alajarin, P. Sanchez-Andrada, Eur. J. Org. Chem. 2006, 1468-1475;
34. b) M. Alajarin, M.-M. Ortin, P. Sanchez-Andrada, A. Vidal, D. Bautista, Org. Lett. 2005, 7, 5281-5284;
35. c) M. Alajarin, P. Sanchez-Andrada, F. P. Cossio, A. Arrieta, B. Lecea, J. Org. Chem. 2001, 66, 8470-8477;
36. d.) M. Alajarin, A. Vidal, P. Sanchez-Andrada, F. Tovar, G. Ochoa, Org. Lett, 2000, 2, 965-968.
37. a) P. Molina, M. Alajarin, A. Arques, R. Benzal, H. Hernandez, J. Chem. Soc., Perkin Trans. 1 1984, 1891-1897;
38. b) P. Molina, M. Alajarin, A. Arques, Synthesis 1982, 596-597.
39. a) M. Alajarin, B. Bonillo, P. Sanchez-Andrada, A. Vidal, D. Bautista, J. Org. Chem. 2007, 72, 5863-5866;
40. b) M. Alajarin, A. Vidal, F. Tovar, Tetrahedron 2005, 61, 1531-1537;
41. c) M. Alajarin, P. Sanchez-Andrada, A. Vidal, F. Tovar, Eur. J. Org. Chem. 2004, 2636-2643;
42. d) M. Alajarin, A. Vidal, F. Tovar, P. Sanchez-Andrada, D. Bautista, Tetrahedron 2003, 59, 9913-9918;
43. e) M. Alajarin, A. Vidal, M.-M. Ortin, F. Tovar, Synthesis 2002, 2393-2398;
44. f) M. Alajarin, A. Vidal, F. Tovar, M. C. Ramirez de Arellano, F. P. Cossio, A. Arrieta, B. Lecea, J. Org. Chem. 2000, 65, 7512-7515;
45. g) F. P. Cossio, A. Arrieta, B. Lecea, M. Alajarin, A. Vidal, F. Tovar, J. Org. Chem. 2000, 65, 3633-3642;
46. h) M. Alajarin, A. Vidal, F. Tovar, C. Conesa, Tetrahedron Lett. 1999, 40, 6127-6130;
47. i) M. Alajarin, P. Molina, A. Vidal, Tetrahedron Lett. 1996, 37, 8945-8948.
48. W. M. F. Fabian, R. Janoschek, J. Am. Chem. Soc. 1997, 119, 4253-4257, and references therein.
49. J. H. Hall, G. Krishnan, J. Org. Chem. 1984, 49, 2498-2500.
50. a) M. Alajarin, B. Bonillo, M. Marin-Luna, A. Vidal, R.-A. Orenes, J. Org. Chem. 2009, 74, 3558-3561
51. b) For a closely related Diels-Aider reaction of a C-vinyl ketenimine with PTAD, see: G. Barbaro, A. Battaglia, P. Giorgianni, J. Org. Chem. 1987, 52, 3289-3296.
52. H. Wamhoff, C. Bamberg, S. Herrmann, M. Nieger, J. Org. Chem. 1994, 59, 3985-3993.
53. The exo-lone-pair effect is a well known electronic effect operating in hetero-Diels-Aider reactions, see: a) M. A. McCarrick, Y.-D. Wu, K. N. Houk, J. Am. Chem. Soc. 1992, 114, 1499-1500;
54. b) M. A. McCarrick, Y.-D. Wu, K.N. Houk, J. Org. Chem. 1993, 58, 3330-3343.
55. Similar results have been reported in computational studies of other Diels-Alder reactions involving HTAD as dienophile, see: a) J. S. Chen, K. N. Houk, C. S. Foote, J. Am. Chem. Soc. 1998, 120, 12303-12309
56. [3d]
57. This stereoelectronic effect has previously been used to account for 6π electrocyclizations of carbodiimides, as well as in hydride transfer reactions, see: a) H. S. Rzepa, P. Molina, M. Alajarin, A. Vidal, Tetrahedron 1992, 48, 7425-7434;
58. b) A. E. Pain, I. H. Williams, Chem. Commun. 1988, 1367-1368;
59. c) I. H. Williams, A. E. Pain, THEOCHEM 1991, 230, 339-347
60. d) A. E. Pain, I. H. Williams, Chem. Commun. 1991, 1417-1418.
61. [3d]
62. The feasibility of a Diels-Alder reaction is related, to the charge-transfer along the bond-forming processes, which corresponds to the more or less polar character of these reactions, see for example: a) L. R. Domingo, M. Arno, I Andres, J. Org. Chem. 1999, 64, 5867-5875
63. b) L. R. Domingo, Tetrahedron 2002, 58, 3765-3774;
64. c) L. R. Domingo, M. J. Aurell, P. Perez, R. Contreras, J. Org. Chem. 2003, 68, 3884-3890.
65. [2c] and: a) J. S. Chen, K. N. Houk, C. S. Foote, J. Am. Chem. Soc, 1998, 120, 12303-12309;
66. b) D. A. Singleton, B. E. Schulmeier, C. Hang, A. A. Thomas, S.-W. Leung, S. R. Merrigan, Tetrahedron 2001, 57, 5149-5160;
67. c) A. G. Leach, K. N. Houk, Chem. Commun. 2002, 1243-1255.
68. a) L. J. Bartolotti, K. Fluchichk, in: Reviews in Computational Chemistry (Eds.: K. B. Lipkowitz, D. B. Boyds), VCH Publishers, New York, 1996, vol.7, pp. 187-216;
69. b) W. Kohn, A. D. Becke, R. G. Parr, J. Phys. Chem. 1996, 100, 12974-12980
70. c) R. G. Parr, R. G. Pearson, J. Am. Chem. Soc. 1983, 105, 7512-7516;
71. d) T. Ziegler, Chem. Rev. 1991, 91, 651-667.
72. M. J. Frisch, G.W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, I C. Burant, I M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, I Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, I B. Cross, C. Adamo, J. Jararnillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, I W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, 11 Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Parkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, I B. Foresman, I V. Ortiz, Q. Cui, Baboul, A. G. Clifford, S. Cioslowski, I Stefanov, B. B. Liu, G. A. Liashenko, P. Piskorz, I. Martin, R. L. Komaromi, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, I A. Pople, Gaussian 03, Revision B.03, Gaussian, Inc., Pittsburgh, PA, 2003.
73. See for example: a) E. Goldstein, B. Beno, K. N. Houk, J. Am. Chem. Soc. 1996, 118, 6036-6043
74. b) O. Wiest, D. C. Montiel, K. N. Houk, J. Phys. Chem. A 1997, 101, 8378-8388;
75. c) J. I. Garcia, V. Martinez-Merino, I A. Mayoral, L. Salvatella, J. Am. Chem. Soc. 1998, 120, 2415-2420;
76. d) L. R. Domingo, M. Arno, J. Andres, J. Am. Chem. Soc. 1998, 120, 1617-1618;
77. e) J. Liu, S. Niwayama, Y. You, K. N. Houk, J. Org. Chem. 1998, 63, 1064-1073;
78. f) D. M. Birney, J. Am. Chem. Soc. 2000, 122, 10917-10925.
79. K. B. Wiberg, Tetrahedron 1968, 24, 1083-1096.
80. a) A. E. Reed, R. B. Weinstock, R Weinhold, J. Chem. Phys. 1985, 83, 735-746;
81. b) A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899-926;
82. c) A. E. Reed, P. v. R. Schleyer, J. Am. Chem. Soc. 1990, 112, 1434-1445.
83. a) W. T. Borden, R. J. Loncharich, K. N. Houk, Annu, Rev. Phys. Chem. 1988, 39, 213-236;
84. b) A. Moyano, M. A. Pericas, E. Valenti, J. Org. Chem. 1989, 54, 573-582;
85. c) These indexes have also been used, to characterize cycloaddition reactions other than [4+2], see for example: B. Lecea, M. Ayerbe, A. Arrieta, R P. Cossio, V. Branchadell, R. M. Ortuño, A. Baceiredo, J. Org. Chem. 2007, 72, 357-366.