Abstract
We have synthesized a series of previously unreported azo dyes via the azo coupling of alkyl substituted dipyrrolopyrazines with aryldiazonium chloride. For this type of substrate where one or both α-positions of the pyrrole rings of the molecules are not occupied by substituents, electrophilic attack was found to occur initially at carbon atom C(3).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
V. I. Terenin, E. L. Ruchkina, A. P. Pleshkova, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 7, 949 (1998).
V. I. Terenin, E. L. Ruchkina, K. V. Karapetyan, V. M. Mamaev, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 11, 1566 (1995).
V. I. Terenin, E. L. Ruchkina, I. F. Leshcheva, A. P. Pleshkova, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 1, 52 (1997).
M. Zupan, V. Stanovnic, and M. Tisler, J. Heterocycl. Chem.,8, 1 (1971).
J. Taylor and D. G. Wibberley, J. Chem. Soc. (C), No. 21, 2693 (1968).
R. Buchan, M. Fraser, and P. V. S. Kong Thoo Lin. J. Org. Chem.,54, 1074 (1989).
Yu. K. Yur'ev, Practical Work in Organic Chemistry [in Russian], Issues 1 and 2, p. 170 (1964).
Additional information
For communication 4 see [1]
M. V. Lomonosov State University, Moscow 119899, Russia Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 236–240, February, 1999.
Rights and permissions
About this article
Cite this article
Terenin, V.I., Borisov, A.V., Ruchkina, E.L. et al. Dipyrrolo[1,2-a; 2′,1′-c]pyrazines. 5. Azo coupling of dipyrrolo[1,2-a;2′,1′-c]pyrazines and 5,6-dihydrodipyrrolo[1,2-a; 2′,1′-c]pyrazines. Chem Heterocycl Compd 35, 211–215 (1999). https://doi.org/10.1007/BF02251713
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02251713