Abstract
Cyanoethylation of 9-phenacyl(β-hydroxy-β-phenylethyl-, or acetamido)-4-azafluorenes under conditions of the Michael reaction occurs regioselectively at position 9. 1-Amino-4-azafluorene under these conditions forms 1-[N,N-di-(β-cyanoethyl)amino)]-(9-β-cyanoethyl)-4-azafluorene. The cyclization of 9-(β-cyanoethyl)-9-phenacyl-4-azafluorene has been carried out into 1′-cyano-2′-phenylspiro[4-aza-fluorene-9,4′-cyclopentene and 1′-imino-2′-hydroxybenzylidenespiro[4-azafluorene-9.3′-cyclopentane]-substituted in the five-membered fragment.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1496–1501, October, 2006.
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Mikhailova, N.M., Levov, A.N., Gozun, S.V. et al. Cyanoethylation of substituted 4-azafluorenes. Synthesis of spiro-[4-azafluorene-9-cyclopentenes]. Chem Heterocycl Compd 42, 1291–1295 (2006). https://doi.org/10.1007/s10593-006-0237-5
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DOI: https://doi.org/10.1007/s10593-006-0237-5