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Alkylation of 1,3-benzothiazin-4-one 2-oxo-, 2-arylimino-, and 2-thioxo derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Sodium salt of 3Н -benzo[e][1,3]thiazine-2,4-dione is easily alkylated at position 3. In the case of 2-(arylimino)-2,3-dihydrobenzo[e][1,3]-thiazin-4-ones, the alkylation reaction at this position occurs regioselectively. Alkylation of 2-thioxo-2,3-dihydrobenzo[e][1,3]thiazin-4-one under the same conditions produced regioisomers, but S-alkylation at the exocyclic sulfur atom occurred in the presence of triethylamine. The reaction of 1-(4-oxo-3,4-dihydrobenzo[e][1,3]thiazin-2-ylidene)guanidine with methyl anthranilate led to the formation of tetracyclic quinazolinо[2,1-b]quinazolinedione.

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This work was performed with financial support from the Ministry of Education and Science of the Russian Federation, within the framework of State Assgnment for Universities scientific activity for years 2014–2016 (project No. 4.2100.2014/K).

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Authors and Affiliations

  1. Voronezh State University, 1 Universitetskaya Sq., Voronezh, 394006, Russia

    Alexandr S. Shestakov, Evgenia O. Zlatoustovskaya, Khidmet S. Shikhaliev, Alexandr V. Falaleev & Oleg E. Sidorenko

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    Mikhail A. Prezent

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  1. Alexandr S. Shestakov
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  2. Mikhail A. Prezent
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  3. Evgenia O. Zlatoustovskaya
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  4. Khidmet S. Shikhaliev
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  5. Alexandr V. Falaleev
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  6. Oleg E. Sidorenko
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Correspondence to Alexandr S. Shestakov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(4), 370–376

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Shestakov, A.S., Prezent, M.A., Zlatoustovskaya, E.O. et al. Alkylation of 1,3-benzothiazin-4-one 2-oxo-, 2-arylimino-, and 2-thioxo derivatives. Chem Heterocycl Comp 51, 370–376 (2015). https://doi.org/10.1007/s10593-015-1709-2

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  • DOI: https://doi.org/10.1007/s10593-015-1709-2

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