Abstract

A method of furo-annulation of 4-hydroxy-2-oxoquinoline-3-carboxylates with 3-arylazirines under Cu(II) catalysis was developed to synthesize a variety of 2,3-dihydrofuro[3,2-c]quinolones bearing a carbamate group at the C2 position. The reaction involves an azirine ring opening across the N-C2 bond and formation of a dihydrofuran ring with the inclusion of two azirine carbon atoms, accompanied by a shift of the ester group to the nitrogen. The discovered reaction is the first example of the use of 2H-azirines for furo-annulation.

Original languageEnglish
Pages (from-to)3615-3619
Number of pages5
JournalOrganic Letters
Volume21
Issue number10
DOIs
Publication statusPublished - 17 May 2019

Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

@article{28ee9c06e4c246d29d2e43d7e800e2a4,
title = "2 H-Azirines as C-C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives",
abstract = "A method of furo-annulation of 4-hydroxy-2-oxoquinoline-3-carboxylates with 3-arylazirines under Cu(II) catalysis was developed to synthesize a variety of 2,3-dihydrofuro[3,2-c]quinolones bearing a carbamate group at the C2 position. The reaction involves an azirine ring opening across the N-C2 bond and formation of a dihydrofuran ring with the inclusion of two azirine carbon atoms, accompanied by a shift of the ester group to the nitrogen. The discovered reaction is the first example of the use of 2H-azirines for furo-annulation.",
author = "Sakharov, {Pavel A.} and Rostovskii, {Nikolai V.} and Khlebnikov, {Alexander F.} and Panikorovskii, {Taras L.} and Novikov, {Mikhail S.}",
year = "2019",
month = "5",
day = "17",
doi = "10.1021/acs.orglett.9b01043",
language = "English",
volume = "21",
pages = "3615--3619",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "10",

}

TY - JOUR

T1 - 2 H-Azirines as C-C Annulation Reagents in Cu-Catalyzed Synthesis of Furo[3,2-c]quinolone Derivatives

AU - Sakharov, Pavel A.

AU - Rostovskii, Nikolai V.

AU - Khlebnikov, Alexander F.

AU - Panikorovskii, Taras L.

AU - Novikov, Mikhail S.

PY - 2019/5/17

Y1 - 2019/5/17

N2 - A method of furo-annulation of 4-hydroxy-2-oxoquinoline-3-carboxylates with 3-arylazirines under Cu(II) catalysis was developed to synthesize a variety of 2,3-dihydrofuro[3,2-c]quinolones bearing a carbamate group at the C2 position. The reaction involves an azirine ring opening across the N-C2 bond and formation of a dihydrofuran ring with the inclusion of two azirine carbon atoms, accompanied by a shift of the ester group to the nitrogen. The discovered reaction is the first example of the use of 2H-azirines for furo-annulation.

AB - A method of furo-annulation of 4-hydroxy-2-oxoquinoline-3-carboxylates with 3-arylazirines under Cu(II) catalysis was developed to synthesize a variety of 2,3-dihydrofuro[3,2-c]quinolones bearing a carbamate group at the C2 position. The reaction involves an azirine ring opening across the N-C2 bond and formation of a dihydrofuran ring with the inclusion of two azirine carbon atoms, accompanied by a shift of the ester group to the nitrogen. The discovered reaction is the first example of the use of 2H-azirines for furo-annulation.

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U2 - 10.1021/acs.orglett.9b01043

DO - 10.1021/acs.orglett.9b01043

M3 - Article

VL - 21

SP - 3615

EP - 3619

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 10

ER -