HETEROCYCLIZATION OF N-PROPENYL-SUBSTITUTED PHENOTHIAZINES AND PHENOXAZINES USING ELECTROPHILES IN AN ANHYDROUS MEDIUM

Authors

  • Е. Е. Сироткина Institute of Petroleum Chemistry, Siberian Branch of the Russian Academy of Sciences, Tomsk 634021
  • А. И. Хлебников I. I. Polzunov Altai State Technical University, Barnaul 656038
  • О. А. Напилкова I. I. Polzunov Altai State Technical University, Barnaul 656038

DOI:

https://doi.org/10.1007/7303

Keywords:

1H-pyrido[3, 2, 1-k, l]phenoxazines, l]phenothiazines, propenyl-substituted, phenoxazine, phenothiazine, heterocyclization, electrophilic catalysts

Abstract

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).

How to Cite
Sirotkina, E. E.; Khlebnikov, A. I.; Napilkova, O. A.  Chem. Heterocycl. Compd. 2008, 44, 1505. [Khim. Geterotsikl. Soedin. 2008, 1855.]

For this article in the English edition see DOI 10.1007/s10593-009-0219-5


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Published

2023-01-05

Issue

No. 12 (2008)

Section

Original Papers