Thermal reactions of N-Alkyl-2-benzylaniline and N-Alkyl-N′-phenyl-o- phenylenediamine: An unusual route to 2-phenylindole and 2-phenylbenzimidazole

Journal of Heterocyclic Chemistry

Volumn 45, Issue 3, 2008, Pages 837-843

  Creencia, Evelyn Cuevas ^a   Taguchi, Kei ^b   Horaguchi, Takaaki ^b  

^a MINDANAO STATE UNIVERSITY ILIGAN INSTITUTE OF TECHNOLOGY   (Philippines)

^b NIIGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 PHENYLINDOLE DERIVATIVE; 2,3 PHENYLINDOLE; ACRIDINE; ANTHRACENE; CALCIUM OXIDE; ENSULIZOLE; N BENZYL 2 BENZYLANILINE; N METHYL 2 BENZYLANILINE; N,N DIBENZYL 2 BENZYLANILINE; N,N DIBENZYL N' PHENYL O PHENYLENEDIAMINE; N,N DIMETHYL 2 BENZYLANILINE; N,N DIMETHYL N' PHENYL O PHENYLENEDIAMINE; PHENAZINE; PHENYLENEDIAMINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DECOMPOSITION; THERMAL ANALYSIS;

EID: 44349154807     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570450331     Document Type: Article

References (55)

1. Creencia, E.C.; Horaguchi, T. J. Heterocycl Chem. 2006, 43, 1441.
2. For references of N-heterocylces with biological activity, see: [a] Chakraborty, D.P.; Roy, R.S. Prog. Chem. Org. Nat. Prod. 1991, 57, 71;
3. [b] Chakraborty, D.P. The Alkaloids 1993, 44, 257;
4. [c] Wu, T.-S.; Wang, M.L.; Wu, P.-L. Phytochemistry 1996, 43, 785;
5. [d] Ho, C.; Katsuno, S.; Ohta, H.; Omura, M.; Kajura, I.; Furukawa, H. Chem. Pharm. Bull. 1997, 45, 48;
6. [e] Wu, T.-S.; Huang, S.-C.; Wu, P.-L. Chem. Pharm. Bull. 1998, 46, 1459;
7. [f] Chakravarty, A.K.; Sarkar, T.; Masuda, K.; Shiojima, K. Phytochemistry 1999, 50, 1263;
8. [g] Ho, C. Natural Medicines (Tokyo) 2000, 54, 117;
9. [h] Ho, C.; Katsuno, S.; Hoigawa, M.; Ruangungsi, N.; Mukainaka, T.; Okuda, M.; Kitigawa, Y.; Tokuda, H.; Nishino, H.; Furukawa, H. J. Nat. Prod. 2000, 63, 125;
10. [i] Tachibana, Y.; Kikuzaki, H.; Lajis, N.H.; Nakatani, N.J. Agric. Food Chem. 2001, 49, 5589;
11. [j] Stolc, S. Life Sci. 1999, 65, 1943;
12. [k] Wang, Y.-S.; He, H.-P.; Shen, Y.-M.; Hong, X.; Jao, X.-J. J. Nat. Prod. 2003, 66, 416;
13. [l] Kuwahara, A.; Nakano, K.; Nozaki, K. J. Org. Chem. 2005, 70, 413;
14. [m] Chiba, T.; Yan, K.; Sugiura, Y. (Toyama Chemical Co., Ltd., Japan) Jpn. Kokai Tokkyo Koho Jp 2005154347, 2005; Chem. Abstr. 2005, 143, 38363.
15. For some references on N-heterocycles in materials, see: [a] Zhang, Y.; Wada, T.; Sasabe, H. J. Mater. Chem. 1998, 8, 809;
16. th ed., Blackwell Science Ltd., U.K., 2000, p.543;
17. [c] Thomas, K.R.J.; Lin, J.T.; Tao, Y.-T.; Ko, C.-W. J. Am. Chem. Soc. 2001, 123, 9404.
18. For some references on the synthesis of indoles, see: [a] Gribble, G.W. Contemp. Org. Synth. 1994, 1, 145;
19. [bl Hughes, D.L. Org. Prep. Proced. Int. 1993, 25, 607;
20. [c] Bartoli, C.; Palmieri, C.; Bosco, M.; Dalpozzo, R. Tetrahedron Lett. 1989, 30, 2129;
21. [d] Scriven, E.F.V.; Turnbull, K. Chem. Rev. 1988, 88, 297;
22. [e] Robinson, B. The Fischer Indole Synthesis, Wiley, Chichester, 1982;
23. [f] Gassman, P.G.; van Bergen, T.J.; Gilbert, D.P.; Cue, B.W. J. Am. Chem. Soc. 1974, 96, 5495;
24. [g] Brown, R.K. In Indoles, Houlihan, W.J. Ed, Wiley-Interscience, New York, 1972;
25. [h] Sundberg, R.J. The Chemistry of Indoles, Academic Press, New York, 1970, chapter 3;
26. [i] Cadogan, J.I.G. Synthesis 1969, 1, 11;
27. [j] Cadogan, J.I.G. Quart. Rev. 1968, 22, 222;
28. [k] Cadogan, J.I.G.; Cameron-Wood, M.; Mackie, R.K.; Searle, R.J.G. J. Chem. Soc. 1965, 4831;
29. [l] Sundberg, R.J. J. Org., Chem. 1965, 30, 3604.
30. For some references on the synthesis of benzimidazoles, see: [a] Wang, Y.; Sarris, K.; Sauer, D.R.; Djuric, S.W. Tetrahedron Lett. 2006, 47, 4823;
31. [b] Trivedi, R.; De, S.K.; Gibbs, R.A. J. Molecular Catalysis A: Chemical 2006, 245, 8;
32. [c] Cee, V.J.; Downing, N.S. Tetrahedron Lett. 2006, 47, 3747;
33. [d] Lin, S.-Y.; Isome, Y.; Stewart, E.; Liu, J.-F.; Yohannes, D.; Yu, L. Tetrahedron Lett. 2006, 47, 2883;
34. [e] Lin, S.; Yang, L. Tetrahedron Lett. 2005, 46, 4315;
35. [f] Gilchrist, T.L. J. Chem. Soc., Perkin Trans. 1 1999, 2849;
36. [g] Perkins, J.J.; Zartman, A.E.; Meissner, R.S. Tetrahedron Lett. 1999, 40, 1103;
37. [h] Carvalho, M.; Lobo, A.M.; Branco, P.S.; Prabhakar, S. Tetrahedron Lett. 1997, 38, 3115;
38. [i] Wang, H.Y.; Partch, R.E.; Li, Y.Z. J. Org. Chem. 1997, 62, 5222;
39. [j] Cadogan, J.I.G.; Marshall, R.; Smith, D.M.; Todd, M.J. J. Chem. Soc. © 1970, 2441;
40. [k] Gilchrist, T.L.; Moody, C.J.; Rees, C.W. J. Chem. Soc., Perkin Trans. 1 1975, 1964.
41. nd ed., Structures, Reactions, Synthesis, and Applications, Wiley-VCH GmbH & Co. KGaA, Weinheim, Germany, 2003, pp 165-170.
42. A radical mechanism is less likely to occur since the temperatures for the thermolysis reactions described in this paper (450°C - 560°C) are not sufficient to bring about the hemolytic cleavage of the N-H, C-H, C-N and C-C bonds. (Smith, M.B. Organic Synthesis, McGraw-Hill, Inc., Singapore, 1994, ch.13.)
43. [8a] Creencia, E.C.; Horaguchi, T. J. Heterocycl. Chem. 2006, 43, 1441;
44. [b] Horaguchi, T.; Oyanagi, T.; Creencia, E.C.; Tanemura, K.; Suzuki, T. J. Heterocycl. Chem. 2004, 41, 1.
45. [9a] Popkins, A.H.; Perretta, C.M.; Selig, R. J. Am. Chem. Soc. 1944, 66, 833-834;
46. [b] Booth, H.; King, F.E.; Parrick, J. J. Chem. Soc. 1958, 2302;
47. [c] Repley, A.R.; Becker, R.H.; Givmanini, A.G. J. Org. Chem. 1971, 36, 1222.
48. [10a] Bartram, C.A.; Harrison, D.; Short, W.F. J. Chem. Soc. 1958, 1158;
49. [b] Schellenberg, K.A. J. Org. Chem. 1963, 28, 3259.
50. Cockborn, W.F.; Johnstone, R.A.W.; Stevens, J.S. J. Chem. Soc. 1960, 3340.
51. [12a] Popkins, A.H.; Perretta, C.M.; Seleg, R. J. Am. Chem. Soc. 1944, 66, 833-834;
52. [b] Booth, H.; King, F.E.; Parrick, J. J. Chem. Soc. 1958, 2302.
53. Cockborn, W.F.; Johnstone, R.A.W.; Stevens, J.S. J. Chem. Soc. 1960, 3340.
54. [14a] Biswas, K.M.; Dhara, R.N.; Mallik, H.; Halder, S.; Sinha-Chaudhuri, A.; Saha, A.; Ganguly, D.; De, P.; Brahmachari, A.S. Monatshefte fur Chemie 1996, 127, 111-116;
55. [b] Furstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117(16), 4468-4475.