Abstract
A theoretical analysis has been carried out of the competing cyclization reactions of 1,2,4-triazahexa-1,3,5-triene and 1,2,4-oxadiazahexa-1,3,5-triene systems using as example C-(arylazo)imines and C-nitrosoimines containing aromatic or aliphatic substituents on the amine nitrogen atom, and also their benzoannelated derivatives.
Similar content being viewed by others
References
Yu. B. Vysotskii and V. S. Bryantsev, Zh. Org. Khim., 38, 1588 (2002).
F. A. Neugebauer and I. Umminger, Chem. Ber., 113, 1205 (1980).
R. Fusko, A. Morchesino, and F. Sannicolo, J. Heterocycl. Chem., 23, 1795 (1986).
G. W. Kirby, Chem. Soc. Rev., 1, 1 (1977).
T. L. Gilchrist, C. J. Harris, J. Moody, and C. W. Rees, J. Chem. Soc., Chem. Commun., 486 (1974).
D. E. Jockman, J. Heterocycl. Chem., 27, 1053 (1990).
B. I. Buzykin, Z. A. Bredikhina, and N. G. Gazetdinova, Zh. Obshch. Khim., 61, 1034 (1991).
B. I. Buzykin, Z. A. Bredikhina, M. P. Sokolov, and N. G. Gazetdinova, Zh. Obshch. Khim., 62, 551 (1992).
B. I. Buzykin and Z. A. Bredikhina, Synthesis, 59 (1993).
K. Paulvannan, T. Chen, and R. Hale, Tetrahedron, 56, 8071 (2000).
K. Paulvannan, R. Hale, D. Sedehi, and T. Chen, Tetrahedron, 57, 9677 (2001).
B. I. Buzykin and O. A. Kharitonova, Zh. Obshch. Khim., 63, 2635 (1993).
B. I. Buzykin and L. P. Sysoeva, Zh. Obshch. Khim., 66, 512 (1996).
B. I. Buzykin, G. D. Lezhnina, and Yu. P. Kitaev, Zh. Org. Khim., 11, 848 (1975).
B. I. Buzykin, G. D. Lezhnina, and Yu. P. Kitaev, Zh. Org. Khim., 11, 1078 (1975).
V. V. Zverev and B. I. Buzykin, Izv. Akad. Nauk, Ser. Khim., 1459 (1995).
K. Fukui and H. Fujimoto, Bull. Chem. Soc. Jpn., 39, 2116 (1966).
V. N. Voshula, Yu. B. Vysotskii, V. I. Seraya, N. T. Novikova, R. Ya. Mushii, and V. I. Dulenko, Khim. Geterotsikl. Soedin., 1623 (1990).
Yu. B. Vysotskii, Teor. Exp. Khim., 17, 469 (1981).
Yu. B. Vysotskii, Zh. Strukt. Khim., 19, 605 (1978).
Yu. B. Vysotskii, Ya. V. Zaikovskaya, I. N. Solonskii, and N. I. Ivanitsyn, Zh. Org. Khim., 31, 732 (1995).
Yu. B. Vysotskii and Ya. V. Zaikovskaya, Zh. Org. Khim., 35, 1464 (1999).
Yu. B. Vysotskii, B. P. Zemskii, T. V. Stupnikova, R. S. Sagitullin, A. N. Kost, and O. P. Shvaika, Khim. Geterotsikl. Soedin., 1496 (1979).
Yu. B. Vysotskii, B. P. Zemskii, T. V. Stupnikova, and R. S. Sagitullin, Khim. Geterotsikl. Soedin., 381 (1980).
Yu. B. Vysotskii, Ya. V. Zaikovskaya, O. I. Kachurin, and V. I. Bratchun, Zh. Org. Khim., 29, 957 (1993).
Yu. B. Vysotskii, Ya. V. Zaikovskaya, O. I. Kachurin, and V. I. Bratchun, Zh. Org. Khim., 29, 964 (1993).
Yu. B. Vysotskii, N. A. Kovach, and O. P. Shvaika, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 3 (1980).
B. I. Buzykin, G. N. Lipunova, L. P. Sysoeva, and L. I. Rusinova, Formazans [in Russian], Nauka, Moscow (1992), p. 208.
Author information
Authors and Affiliations
Additional information
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 373–385, March, 2006.
Rights and permissions
About this article
Cite this article
Vysotskii, Y.B., Buzykin, B.I. & Bryantsev, V.S. Quantum-chemical interpretation of cyclization and recyclization reactions. 27. Electrocyclization of phenyl derivatives and benzoannelated derivatives of 1,2,4-triazahexa-1,3,5-triene and 1,2,4-oxadiazahexa-1,3,5-triene. Chem Heterocycl Compd 42, 331–342 (2006). https://doi.org/10.1007/s10593-006-0090-6
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10593-006-0090-6
Keywords
- C-(arylazo)imines
- 1,2,4-hexatrienes
- 1,4-dihydro-1,2,4-benzoxadiazine
- 1,4-dihydro-1,2,4-benzotriazine
- C-nitrosoimines
- 1,2,4-oxadiaza-1,3,5-hexatrienes
- 1,2,4-oxadiazoles
- 4-phenyl-and 4-alkyl-1,2,4-oxadiaza-1,3-butadienes
- 1-phenyl-and 1-alkyl-1,2,4-triaza-1,3-butadienes
- 1,2,4-triazole
- formazans
- formazenes
- quantum-chemical calculation
- competing reactions
- pericyclic reactions
- semiempirical methods
- sigmatropy
- electrocyclization