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

Александр С. Шестаков, Михаил А. Презент, Евгения О. Златоустовская, Хидмет С. Шихалиев, Александр В. Фалалеев, Олег Е. Сидоренко
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Abstract


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-4one 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.

How to Cite
Shestakov, A. S.; Prezent, M. A.; Zlatoustovskaya, E. O.; Shikhaliev, K. S.; Falaleev, A. V.; Sidorenko, O. E. Chem. Heterocycl. Compd. 2015, 51, 370. [Khim. Geterotsikl. Soedin. 2015, 51, 370.]

For this article in the English edition see DOI 10.1007/s10593-015-1709-2


Keywords


2-(arylimino)-2,3-dihydrobenzo[e][1,3]thiazin-4-one; 3H-benzo[e][1,3]thiazine-2,4-dione; benzo[e][1,3]thiazin-4-one; 2thioxo-2,3-dihydrobenzo[e][1,3]thiazin-4-one; alkylation

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