Metal carbonyl mediated rearrangement of 5-(2-oxoalkyl)-1,2,4-oxadiazoles: Synthesis of fully substituted pyrimidines.

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Metal carbonyl mediated rearrangement of 5-(2-oxoalkyl)-1,2,4-oxadiazoles: Synthesis of fully substituted pyrimidines. / Galenko, Ekaterina E. ; Zanakhov, Timur O. ; Novikov, Mikhail S. ; Khlebnikov, Alexander F. .

In: Organic & Biomolecular Chemistry, Vol. 21, No. 14, 2023, p. 2990-3001.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{cb4c773862114a41acae423b51ab9d48,

title = "Metal carbonyl mediated rearrangement of 5-(2-oxoalkyl)-1,2,4-oxadiazoles: Synthesis of fully substituted pyrimidines.",

abstract = "Variously substituted ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxylates can be easily prepared by a metal carbonyl mediated rearrangement of ethyl 3-oxo-2-(1,2,4-oxadiazol-5-yl)propanoates. The irradiation of a mixture of oxadiazoles and Fe(CO)5 in wet solvents with a 365 nm LED at room temperature for 2 h followed by heating at 80 °C for 2 h gives pyrimidines in up to 90% yield. This procedure enables the preparation of 6-oxo-1,6-dihydropyrimidine-5-carboxylates with various aryl substituents at the C2 and alkyl or aryl substituents at the C4 position. 1-(1,2,4-Oxadiazol-5-yl)propan-2-ones analogously give 6-methylpyrimidin-4(3H)-ones, albeit in lower yields. Ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxylates can be easily modified at the C6 position by bromination followed by cross-coupling reactions to give pyrimidine-5-carboxylates with pyridyl, amino and ethynyl substituents.",

author = "Galenko, {Ekaterina E.} and Zanakhov, {Timur O.} and Novikov, {Mikhail S.} and Khlebnikov, {Alexander F.}",

year = "2023",

doi = "10.1039/D3OB00148B",

language = "English",

volume = "21",

pages = "2990--3001",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "14",

}

RIS

TY - JOUR

T1 - Metal carbonyl mediated rearrangement of 5-(2-oxoalkyl)-1,2,4-oxadiazoles: Synthesis of fully substituted pyrimidines.

AU - Galenko, Ekaterina E.

AU - Zanakhov, Timur O.

AU - Novikov, Mikhail S.

AU - Khlebnikov, Alexander F.

PY - 2023

Y1 - 2023

N2 - Variously substituted ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxylates can be easily prepared by a metal carbonyl mediated rearrangement of ethyl 3-oxo-2-(1,2,4-oxadiazol-5-yl)propanoates. The irradiation of a mixture of oxadiazoles and Fe(CO)5 in wet solvents with a 365 nm LED at room temperature for 2 h followed by heating at 80 °C for 2 h gives pyrimidines in up to 90% yield. This procedure enables the preparation of 6-oxo-1,6-dihydropyrimidine-5-carboxylates with various aryl substituents at the C2 and alkyl or aryl substituents at the C4 position. 1-(1,2,4-Oxadiazol-5-yl)propan-2-ones analogously give 6-methylpyrimidin-4(3H)-ones, albeit in lower yields. Ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxylates can be easily modified at the C6 position by bromination followed by cross-coupling reactions to give pyrimidine-5-carboxylates with pyridyl, amino and ethynyl substituents.

AB - Variously substituted ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxylates can be easily prepared by a metal carbonyl mediated rearrangement of ethyl 3-oxo-2-(1,2,4-oxadiazol-5-yl)propanoates. The irradiation of a mixture of oxadiazoles and Fe(CO)5 in wet solvents with a 365 nm LED at room temperature for 2 h followed by heating at 80 °C for 2 h gives pyrimidines in up to 90% yield. This procedure enables the preparation of 6-oxo-1,6-dihydropyrimidine-5-carboxylates with various aryl substituents at the C2 and alkyl or aryl substituents at the C4 position. 1-(1,2,4-Oxadiazol-5-yl)propan-2-ones analogously give 6-methylpyrimidin-4(3H)-ones, albeit in lower yields. Ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxylates can be easily modified at the C6 position by bromination followed by cross-coupling reactions to give pyrimidine-5-carboxylates with pyridyl, amino and ethynyl substituents.

UR - https://www.mendeley.com/catalogue/6b8633ee-fe8b-39e5-8536-731c2077fb8b/

U2 - 10.1039/D3OB00148B

DO - 10.1039/D3OB00148B

M3 - Article

VL - 21

SP - 2990

EP - 3001

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 14

ER -

ID: 107200663