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Nitrosation of 5H-thiazolo[3,2-a]pyrimidin-3(2H)-ones

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-ones with sodium nitrite in acetic acid at room temperature gave 2-(hydroxyimino)-5Н-thiazolo[3,2-a]pyrimidin-3(2Н)-ones, which exist as a single isomer according to NMR data. Calculations by the B3LYP/6-311++G(d,p) method indicated that the Е-isomer of hydroxyimino derivative was favored by 15.7 kJ/mol over the Z-isomer.

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This work was performed with financial support from the Ministry of Education and Science of the Russian Federation (contract No. 14.577.21.0137, unique identifier PNIER REMEFI57714X0137) by using scientific equipment of the Collective Use Center "Investigation of Physicochemical Properties of Substances and Materials" at Samara State Technical University.

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  1. Samara State Technical University, 244 Molodogvardeyskaya St., Samara, 443100, Russia

    Evgenia A. Lashmanova & Andrey K. Shiryaev

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  1. Evgenia A. Lashmanova
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  2. Andrey K. Shiryaev
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Correspondence to Andrey K. Shiryaev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(4), 377–380

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Lashmanova, E.A., Shiryaev, A.K. Nitrosation of 5H-thiazolo[3,2-a]pyrimidin-3(2H)-ones. Chem Heterocycl Comp 51, 377–380 (2015). https://doi.org/10.1007/s10593-015-1710-9

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