Direction of the Reaction of 6-Methylpyrimidine-2,4(1H,3H)-dione with 2-Chloromethylthiirane: N1- or N3-Thietanyl Derivative?


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The reaction of 6-methylpyrimidine-2,41H,3H-dione with 2-chloromethylthiirane gave 6-methyl-N-thietan-3-ylpyrimidine-2,41H,3H-dione. Its oxidation subsequent reaction of the resulting N-1,1-dioxo-λ6-thietan-3-yl derivative with ethyl chloroacetate afforded the corresponding ethyl pyrimidinylacetate. The structure of the latter was determined by X-ray analysis, which confirmed the formation of N3-thietan-3-yl derivative rather than its N1-substituted isomer in the title reaction. According to the results of B3LYP/6-31G++d,p, PBE/3ζ, MP2/6-31G++d,p quantum chemical calculations,the N3-thietanyl derivative is more stable than the N1-isomer. It was also found that the calculated barrier to internal rotation of the thietanyl group about the N–C bond in 6-methyl-3-thietan-3-yl-pyrimidine-2,41H,3H-dione is lower than in the N1-isomer.

作者简介

V. Kataev

Bashkir State Medical University

Email: kuzmaggy@mail.ru
俄罗斯联邦, ul. Lenina 3, Ufa, 450000 Bashkortostan

S. Meshcheryakova

Bashkir State Medical University

Email: kuzmaggy@mail.ru
俄罗斯联邦, ul. Lenina 3, Ufa, 450000 Bashkortostan

E. Meshcheryakova

Institute of Petrochemistry and Catalysis

Email: kuzmaggy@mail.ru
俄罗斯联邦, pr. Oktyabrya 141, Ufa, 450075 Bashkortostan

T. Tyumkina

Institute of Petrochemistry and Catalysis

Email: kuzmaggy@mail.ru
俄罗斯联邦, pr. Oktyabrya 141, Ufa, 450075 Bashkortostan

L. Khalilov

Institute of Petrochemistry and Catalysis

Email: kuzmaggy@mail.ru
俄罗斯联邦, pr. Oktyabrya 141, Ufa, 450075 Bashkortostan

V. Lazarev

Ufa State Aviation Technical University

Email: kuzmaggy@mail.ru
俄罗斯联邦, ul. K. Marksa 12, Ufa, 450008 Bashkortostan

V. Kuznetsov

Ufa State Aviation Technical University; Ufa State Petroleum Technological University

编辑信件的主要联系方式.
Email: kuzmaggy@mail.ru
俄罗斯联邦, ul. K. Marksa 12, Ufa, 450008 Bashkortostan; ul. Kosmonavtov 1, Ufa, 450062 Bashkortostan

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