An efficient synthesis of functionalized 2H-1,3,5-oxadiazines via metal-carbenoid-induced 1,2,4-oxadiazole ring cleavage

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An efficient synthesis of functionalized 2H-1,3,5-oxadiazines via metal-carbenoid-induced 1,2,4-oxadiazole ring cleavage. / Strelnikova, Julia O.; Rostovskii, Nikolai V.; Khoroshilova, Olesya V.; Khlebnikov, Alexander F.; Novikov, Mikhail S.

в: Synthesis (Germany), Том 53, № 2, ss-2020-n0194-op, 19.01.2021, стр. 348-358.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{c50e7c8c730246a2a6cb0ae4ca47e2c0,

title = "An efficient synthesis of functionalized 2H-1,3,5-oxadiazines via metal-carbenoid-induced 1,2,4-oxadiazole ring cleavage",

abstract = "A high-yielding method for the synthesis of 2H-1,3,5-oxadi-azines by rhodium(II)- or copper(II)-catalyzed reaction of 1,2,4-oxadi-azoles with α-diazo esters has been developed. The reaction proceeds via attack of the metallocarbenoid on the oxadiazole N2 atom followed by ring opening/1,6-electrocyclization and enables the introduction of alkyl, aryl, oxy, and amino substituents into the 6-position and electron-withdrawing groups into the 2-position of 1,3,5-oxadiazine. The N2-attack and the N4-attack of the carbenoid cause different oxadiazole ring openings, which are controlled by the substitution at C5. The presence of a substituent at this position is a prerequisite for the N2-attack to occur, leading to the formation of 1,3,5-oxadiazines.",

keywords = "Carbenoids, Catalysis, Diazo compounds, Oxadiazines, Oxadiazoles, Rhodium, ROUTE, 2H-AZIRINES, AMIDOXIMES, BUILDING-BLOCKS, catalysis, FORMAL 3+2 CYCLOADDITION, ISOXAZOLES, 3,5-DISUBSTITUTED-1,2,4-OXADIAZOLES, ESTERS, CHEMISTRY, oxadiazoles, H INSERTION, carbenoids, diazo compounds, oxadiazines, rhodium",

author = "Strelnikova, {Julia O.} and Rostovskii, {Nikolai V.} and Khoroshilova, {Olesya V.} and Khlebnikov, {Alexander F.} and Novikov, {Mikhail S.}",

year = "2021",

month = jan,

day = "19",

doi = "10.1055/s-0040-1707278",

language = "English",

volume = "53",

pages = "348--358",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "2",

}

RIS

TY - JOUR

T1 - An efficient synthesis of functionalized 2H-1,3,5-oxadiazines via metal-carbenoid-induced 1,2,4-oxadiazole ring cleavage

AU - Strelnikova, Julia O.

AU - Rostovskii, Nikolai V.

AU - Khoroshilova, Olesya V.

AU - Khlebnikov, Alexander F.

AU - Novikov, Mikhail S.

PY - 2021/1/19

Y1 - 2021/1/19

N2 - A high-yielding method for the synthesis of 2H-1,3,5-oxadi-azines by rhodium(II)- or copper(II)-catalyzed reaction of 1,2,4-oxadi-azoles with α-diazo esters has been developed. The reaction proceeds via attack of the metallocarbenoid on the oxadiazole N2 atom followed by ring opening/1,6-electrocyclization and enables the introduction of alkyl, aryl, oxy, and amino substituents into the 6-position and electron-withdrawing groups into the 2-position of 1,3,5-oxadiazine. The N2-attack and the N4-attack of the carbenoid cause different oxadiazole ring openings, which are controlled by the substitution at C5. The presence of a substituent at this position is a prerequisite for the N2-attack to occur, leading to the formation of 1,3,5-oxadiazines.

AB - A high-yielding method for the synthesis of 2H-1,3,5-oxadi-azines by rhodium(II)- or copper(II)-catalyzed reaction of 1,2,4-oxadi-azoles with α-diazo esters has been developed. The reaction proceeds via attack of the metallocarbenoid on the oxadiazole N2 atom followed by ring opening/1,6-electrocyclization and enables the introduction of alkyl, aryl, oxy, and amino substituents into the 6-position and electron-withdrawing groups into the 2-position of 1,3,5-oxadiazine. The N2-attack and the N4-attack of the carbenoid cause different oxadiazole ring openings, which are controlled by the substitution at C5. The presence of a substituent at this position is a prerequisite for the N2-attack to occur, leading to the formation of 1,3,5-oxadiazines.

KW - Carbenoids

KW - Catalysis

KW - Diazo compounds

KW - Oxadiazines

KW - Oxadiazoles

KW - Rhodium

KW - ROUTE

KW - 2H-AZIRINES

KW - AMIDOXIMES

KW - BUILDING-BLOCKS

KW - catalysis

KW - FORMAL 3+2 CYCLOADDITION

KW - ISOXAZOLES

KW - 3,5-DISUBSTITUTED-1,2,4-OXADIAZOLES

KW - ESTERS

KW - CHEMISTRY

KW - oxadiazoles

KW - H INSERTION

KW - carbenoids

KW - diazo compounds

KW - oxadiazines

KW - rhodium

UR - http://www.scopus.com/inward/record.url?scp=85092457119&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/ca91b0b3-5e56-3b5c-acea-d222cb7c48aa/

U2 - 10.1055/s-0040-1707278

DO - 10.1055/s-0040-1707278

M3 - Article

AN - SCOPUS:85092457119

VL - 53

SP - 348

EP - 358

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 2

M1 - ss-2020-n0194-op

ER -

ID: 70611945