Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement

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Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement. / Tiuftiakov, Nikolai Yu; Strelnikova, Julia O.; Filippov, Ilya P.; Khaidarov, Adel R.; Khlebnikov, Alexander F.; Bunev, Alexander S.; Novikov, Mikhail S.; Rostovskii, Nikolai V.

In: Organic Letters, Vol. 23, No. 17, 23.08.2021, p. 6998-7002.

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

BibTeX

@article{1ca27c3968f94585a62c1fcbb02616a7,

title = "Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement",

abstract = "A one-step synthesis of cytotoxic 2-aroylpyrimidines by the denitrogenative reaction of 1-tosyl-1,2,3-triazoles with isoxazoles under rhodium catalysis has been developed. According to the density functional theory calculations and control experiments, the disclosed reaction proceeds via the rearrangement of an oxadiazatetraene intermediate involving a cascade of intramolecular aza-Diels-Alder and retro-aza-Diels-Alder reactions. The presence of a substituent at C4 of the isoxazole is a prerequisite for the formation of the pyrimidines. ",

author = "Tiuftiakov, {Nikolai Yu} and Strelnikova, {Julia O.} and Filippov, {Ilya P.} and Khaidarov, {Adel R.} and Khlebnikov, {Alexander F.} and Bunev, {Alexander S.} and Novikov, {Mikhail S.} and Rostovskii, {Nikolai V.}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = aug,

day = "23",

doi = "10.1021/acs.orglett.1c02706",

language = "English",

volume = "23",

pages = "6998--7002",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

RIS

TY - JOUR

T1 - Rhodium-Catalyzed Synthesis of 2-Aroylpyrimidines via Cascade Heteropolyene Rearrangement

AU - Tiuftiakov, Nikolai Yu

AU - Strelnikova, Julia O.

AU - Filippov, Ilya P.

AU - Khaidarov, Adel R.

AU - Khlebnikov, Alexander F.

AU - Bunev, Alexander S.

AU - Novikov, Mikhail S.

AU - Rostovskii, Nikolai V.

PY - 2021/8/23

Y1 - 2021/8/23

N2 - A one-step synthesis of cytotoxic 2-aroylpyrimidines by the denitrogenative reaction of 1-tosyl-1,2,3-triazoles with isoxazoles under rhodium catalysis has been developed. According to the density functional theory calculations and control experiments, the disclosed reaction proceeds via the rearrangement of an oxadiazatetraene intermediate involving a cascade of intramolecular aza-Diels-Alder and retro-aza-Diels-Alder reactions. The presence of a substituent at C4 of the isoxazole is a prerequisite for the formation of the pyrimidines.

AB - A one-step synthesis of cytotoxic 2-aroylpyrimidines by the denitrogenative reaction of 1-tosyl-1,2,3-triazoles with isoxazoles under rhodium catalysis has been developed. According to the density functional theory calculations and control experiments, the disclosed reaction proceeds via the rearrangement of an oxadiazatetraene intermediate involving a cascade of intramolecular aza-Diels-Alder and retro-aza-Diels-Alder reactions. The presence of a substituent at C4 of the isoxazole is a prerequisite for the formation of the pyrimidines.

UR - http://www.scopus.com/inward/record.url?scp=85114600091&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.1c02706

DO - 10.1021/acs.orglett.1c02706

M3 - Article

AN - SCOPUS:85114600091

VL - 23

SP - 6998

EP - 7002

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 17

ER -

ID: 87468073