10-Propenylphenothiazine reacts with a catalytic amount of BF3·Et2O in dry ethyl acetate via intramolecular heterocyclization of an intermediate dimeric cation to give mainly 1-ethyl-2-methyl-3-(phenothiazin-10-yl)-2,3-dihydro-1H-pyrido[3,2,1-k,l]phenothiazine and a minor product through fission of phenothiazine which is 1-ethyl-2-methyl-1H-pyrido[3,2,1-k,l]phenothiazine. Under similar conditions 10-propenylphenoxazine gave an oligomer (degree of polymerization 4.4) and the minor product 1-ethyl-2-methyl-1H-pyrido[3,2,1-k,l]phenoxazine likely formed similarly to the phenothiazine analog from the corresponding product of intramolecular heterocyclization (the latter not being observed in the reaction mixture).
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Dedicated to Academician of the Russian Academy of Sciences B. A. Trofimov on his jubilee.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1855–1860, December, 2008.
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Sirotkina, E.E., Khlebnikov, A.I. & Napilkova, O.A. Heterocyclization of N-propenyl-substituted phenothiazines and phenoxazines using electrophiles in an anhydrous medium. Chem Heterocycl Comp 44, 1505–1509 (2008). https://doi.org/10.1007/s10593-009-0219-5
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DOI: https://doi.org/10.1007/s10593-009-0219-5