A new synthesis of 5-hydroxy-6-methyluracil
Publication type: Journal Article
Publication date: 2012-11-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Dehydration of 5,6-dihydro-5,6-dihydroxy-6-methyl- and 5,6-dihydro-5,6-dihydroxy-1,3,6-trimethyl-uracil in 0.4 M aqueous sulfuric acid gives 5-hydroxy-6-methyl- and 5-hydroxy-1,3,6-trimethyluracil in quantitative yields. Two possible mechanisms have been examined using the mPW1k/6-311+G(2df,2pd)//mPW1k/6-31+G(d,p) method for the transformation of methylated and non-methylated 5,6-dihydro-5,6-dihydroxy-6-methyluracils into the corresponding 5-hydroxy-6-methyluracils. The first is a hydride C5–C6 shift occurring in concert with the loss of a water molecule and formation of the corresponding protonated 5,6-dihydro-5-oxo-6-methyluracils. The second is an acid-catalyzed dehydration reaction to yield 5-hydroxy-6-methyluracils. The calculations demonstrated that the second pathway was energetically most favorable.
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Grabovskiy S. A., Murinov Y. I., Kabal'nova N. N. A new synthesis of 5-hydroxy-6-methyluracil // Tetrahedron Letters. 2012. Vol. 53. No. 45. pp. 6025-6028.
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Grabovskiy S. A., Murinov Y. I., Kabal'nova N. N. A new synthesis of 5-hydroxy-6-methyluracil // Tetrahedron Letters. 2012. Vol. 53. No. 45. pp. 6025-6028.
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TY - JOUR
DO - 10.1016/j.tetlet.2012.08.133
UR - https://doi.org/10.1016/j.tetlet.2012.08.133
TI - A new synthesis of 5-hydroxy-6-methyluracil
T2 - Tetrahedron Letters
AU - Grabovskiy, Stanislav A.
AU - Murinov, Yuri I
AU - Kabal'nova, Natalia N.
PY - 2012
DA - 2012/11/01
PB - Elsevier
SP - 6025-6028
IS - 45
VL - 53
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2012_Grabovskiy,
author = {Stanislav A. Grabovskiy and Yuri I Murinov and Natalia N. Kabal'nova},
title = {A new synthesis of 5-hydroxy-6-methyluracil},
journal = {Tetrahedron Letters},
year = {2012},
volume = {53},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/j.tetlet.2012.08.133},
number = {45},
pages = {6025--6028},
doi = {10.1016/j.tetlet.2012.08.133}
}
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MLA
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Grabovskiy, Stanislav A., et al. “A new synthesis of 5-hydroxy-6-methyluracil.” Tetrahedron Letters, vol. 53, no. 45, Nov. 2012, pp. 6025-6028. https://doi.org/10.1016/j.tetlet.2012.08.133.
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