Isomerization of 5-(2H-azirin-2-yl)oxazoles

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Isomerization of 5-(2H-azirin-2-yl)oxazoles : An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles. / Zanakhov, Timur O.; Galenko, Ekaterina E.; Kryukova, Mariya A.; Novikov, Mikhail S.; Khlebnikov, Alexander A.

In: Molecules, Vol. 26, No. 7, 1881, 26.03.2021.

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

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@article{9b5b58cdcb974a72ac40b6b8dfacd7ef,

title = "Isomerization of 5-(2H-azirin-2-yl)oxazoles: An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles",

abstract = "An atom economical method for the preparation of variously substituted 4H-pyrrolo[2,3-d]oxazoles was developed on the basis of thermal isomerization of 5-(2H-azirin-2-yl)oxazoles. The lat-ter were prepared by Rh2 (oct)4 catalyzed reaction of 2-(3-aryl/heteroaryl)-2-diazoacetyl-2H-azirines with a set of substituted acetonitriles, benzonitriles, acrylonitrile and fumaronitrile. According to DFT calculations the transformation of 5-(2H-azirin-2-yl)oxazole to 4H-pyrrolo[2,3-d]oxazole occurs through the nitrenoid-like transition state to give a 3aH-pyrrolo[2,3-d]oxazole intermediate, followed by 1,5-H-shift.",

keywords = "Azirine, Diazo compounds, Isomerization, Oxazole, Pyrrolo[2,3-d]oxazole, isomerization, azirine, 3-d]oxazole, diazo compounds, pyrrolo[2, oxazole",

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

note = "Publisher Copyright: {\textcopyright} 2021 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2021",

month = mar,

day = "26",

doi = "10.3390/molecules26071881",

language = "English",

volume = "26",

journal = "Molecules",

issn = "1420-3049",

publisher = "MDPI AG",

number = "7",

}

RIS

TY - JOUR

T1 - Isomerization of 5-(2H-azirin-2-yl)oxazoles

T2 - An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles

AU - Zanakhov, Timur O.

AU - Galenko, Ekaterina E.

AU - Kryukova, Mariya A.

AU - Novikov, Mikhail S.

AU - Khlebnikov, Alexander A.

PY - 2021/3/26

Y1 - 2021/3/26

N2 - An atom economical method for the preparation of variously substituted 4H-pyrrolo[2,3-d]oxazoles was developed on the basis of thermal isomerization of 5-(2H-azirin-2-yl)oxazoles. The lat-ter were prepared by Rh2 (oct)4 catalyzed reaction of 2-(3-aryl/heteroaryl)-2-diazoacetyl-2H-azirines with a set of substituted acetonitriles, benzonitriles, acrylonitrile and fumaronitrile. According to DFT calculations the transformation of 5-(2H-azirin-2-yl)oxazole to 4H-pyrrolo[2,3-d]oxazole occurs through the nitrenoid-like transition state to give a 3aH-pyrrolo[2,3-d]oxazole intermediate, followed by 1,5-H-shift.

AB - An atom economical method for the preparation of variously substituted 4H-pyrrolo[2,3-d]oxazoles was developed on the basis of thermal isomerization of 5-(2H-azirin-2-yl)oxazoles. The lat-ter were prepared by Rh2 (oct)4 catalyzed reaction of 2-(3-aryl/heteroaryl)-2-diazoacetyl-2H-azirines with a set of substituted acetonitriles, benzonitriles, acrylonitrile and fumaronitrile. According to DFT calculations the transformation of 5-(2H-azirin-2-yl)oxazole to 4H-pyrrolo[2,3-d]oxazole occurs through the nitrenoid-like transition state to give a 3aH-pyrrolo[2,3-d]oxazole intermediate, followed by 1,5-H-shift.

KW - Azirine

KW - Diazo compounds

KW - Isomerization

KW - Oxazole

KW - Pyrrolo[2,3-d]oxazole

KW - isomerization

KW - azirine

KW - 3-d]oxazole

KW - diazo compounds

KW - pyrrolo[2

KW - oxazole

UR - http://www.scopus.com/inward/record.url?scp=85103920374&partnerID=8YFLogxK

U2 - 10.3390/molecules26071881

DO - 10.3390/molecules26071881

M3 - Article

C2 - 33810476

AN - SCOPUS:85103920374

VL - 26

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 7

M1 - 1881

ER -

ID: 77219762

Isomerization of 5-(2H-azirin-2-yl)oxazoles: An atom-economic approach to 4H-pyrrolo[2,3-d]oxazoles

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