Abstract
Stable diazo compounds of the azafluorene series, viz., 9-diazo-4-azafluorenone and 1,3-diphenyl-4-azafluorene, were obtained from 4-azafluorenone and 1,3-diphenyl-4-azafluorene tosylhydrazones. 1′,2′-Dicarbomethoxyspiro(4-azafluorene-9,3′-cyclopropane) was obtained from 4-azafluorenone tosylhydrazone, and 4′,5′-dicarbomethoxyspiro(4-azafluorene-9,3′-pyrazolenine) was obtained from 9-diazo-4-azafluorene. It is assumed that the product in the latter case is obtained as a result of reaction of a carbene, viz., 4-azafluorenylidene carbene, which is formed from 9-diazo-4-fluorene, with dimethyl acetylenedicarboxylate.
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A. K. Colter and S. S. Wang, J. Org. Chem., 27, 1517 (1962).
N. S. Prostakov, A. V. Varlamov, G. A. Vasil'ev, O. G. Kesarev, and G. A. Urbina, Khim. Geterotsikl. Soedin., No. 1, 124 (1977).
N. S. Prostakov, A. V. Varlamov, G. A. Vasil'ev, V. P. Zvolinskii, O. I. Sorokin, and N. D. Lopatina, Khim. Geterotsikl. Soedin., No. 8, 1112 (1975).
C. Tuchscherer, M. Bruch, and D. Rewiki, Tetrahedron Lett., No. 11, 865 (1973).
N. Filipescu and S. R. de Member, Tetrahedron, 24, No. 14, 5181 (1968).
T. Mukai, T. Nakazawa, and K. Isobe, Tetrahedron Lett., No. 5, 565 (1968).
E. Funakubo, I. Moritani, and T. Nagai, Tetrahedron Lett., No. 16, 1069 (1963).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 951–953, July, 1979.
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Prostakov, N.S., Anisimov, B.N., Varlamov, A.V. et al. Synthesis of 9-diazo-4-azafluorenes. Chem Heterocycl Compd 15, 777–780 (1979). https://doi.org/10.1007/BF00473562
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DOI: https://doi.org/10.1007/BF00473562