Synthesis and photochromism of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones

Nina A. Larina; Vladimir Lokshin; Jerome Berthet; Stephanie Delbaere; Gaston Vermeersch; Vladimir Khodorkovsky

doi:10.1016/j.tet.2010.08.039

Synthesis and photochromism of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones

Nina A. Larina, Vladimir Lokshin, Jerome Berthet, Stephanie Delbaere, Gaston Vermeersch, Vladimir Khodorkovsky

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

8 Scopus citations

Abstract

Synthesis and characterization of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones is described. In addition to their potential biological activity, these compounds exhibit photoreversible photochromic properties in anaerobic conditions. Using the 1 and 2D NMR techniques we demonstrated that the coloration occurred owing to the formation of fluorescent 5a,6-dihydrobenzo[b]acridin-(5H)-ones. The photoreaction is stereoselective and the S,R-isomers are the major products (83%) whereas the S,S-isomers are the minor (6%). In addition, the irreversible formation of two oxidation products, 3-(2-benzoylbenzoyl)quinolin-4(1H)-ones, and acridin-12(5H)-one derivatives was observed in the presence of air.

Original language	English
Pages (from-to)	8291-8299
Number of pages	9
Journal	Tetrahedron
Volume	66
Issue number	42
DOIs	https://doi.org/10.1016/j.tet.2010.08.039
State	Published - 16 Oct 2010
Externally published	Yes

Keywords

Acridine
Fluorescence
Hydrogen bonding
Photochromism
Quinolin-4(1H)-one

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2010.08.039

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@article{506ee25b05534f2290cc1b7dc0a4d9a8,

title = "Synthesis and photochromism of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones",

abstract = "Synthesis and characterization of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones is described. In addition to their potential biological activity, these compounds exhibit photoreversible photochromic properties in anaerobic conditions. Using the 1 and 2D NMR techniques we demonstrated that the coloration occurred owing to the formation of fluorescent 5a,6-dihydrobenzo[b]acridin-(5H)-ones. The photoreaction is stereoselective and the S,R-isomers are the major products (83%) whereas the S,S-isomers are the minor (6%). In addition, the irreversible formation of two oxidation products, 3-(2-benzoylbenzoyl)quinolin-4(1H)-ones, and acridin-12(5H)-one derivatives was observed in the presence of air.",

keywords = "Acridine, Fluorescence, Hydrogen bonding, Photochromism, Quinolin-4(1H)-one",

author = "Larina, {Nina A.} and Vladimir Lokshin and Jerome Berthet and Stephanie Delbaere and Gaston Vermeersch and Vladimir Khodorkovsky",

note = "Funding Information: This work was supported by the Centre National de la Recherche Scientifique (CNRS). The 300 and 500 MHz NMR facilities were funded by the R{\'e}gion Nord-Pas de Calais (France) , the Minist{\`e}re de la Jeunesse de l′Education Nationale et de la Recherche (MJENR) , and the Fonds Europ{\'e}ens de D{\'e}veloppement R{\'e}gional (FEDER) . Part of this collaborative work was realized within the framework of the International Research Group IRG CNRS 93 {\textquoteleft}Phenics{\textquoteright} (Photoswitchable Organic Molecular Systems & Devices). N.A.L. is thankful for the PhD fellowship to the {\textquoteleft}Reseau Formation-Recherche Franco-Russe{\textquoteright} of the French Ministry for Education and Research. ",

year = "2010",

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day = "16",

doi = "10.1016/j.tet.2010.08.039",

language = "English",

volume = "66",

pages = "8291--8299",

journal = "Tetrahedron",

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TY - JOUR

T1 - Synthesis and photochromism of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones

AU - Larina, Nina A.

AU - Lokshin, Vladimir

AU - Berthet, Jerome

AU - Delbaere, Stephanie

AU - Vermeersch, Gaston

AU - Khodorkovsky, Vladimir

N1 - Funding Information: This work was supported by the Centre National de la Recherche Scientifique (CNRS). The 300 and 500 MHz NMR facilities were funded by the Région Nord-Pas de Calais (France) , the Ministère de la Jeunesse de l′Education Nationale et de la Recherche (MJENR) , and the Fonds Européens de Développement Régional (FEDER) . Part of this collaborative work was realized within the framework of the International Research Group IRG CNRS 93 ‘Phenics’ (Photoswitchable Organic Molecular Systems & Devices). N.A.L. is thankful for the PhD fellowship to the ‘Reseau Formation-Recherche Franco-Russe’ of the French Ministry for Education and Research.

PY - 2010/10/16

Y1 - 2010/10/16

N2 - Synthesis and characterization of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones is described. In addition to their potential biological activity, these compounds exhibit photoreversible photochromic properties in anaerobic conditions. Using the 1 and 2D NMR techniques we demonstrated that the coloration occurred owing to the formation of fluorescent 5a,6-dihydrobenzo[b]acridin-(5H)-ones. The photoreaction is stereoselective and the S,R-isomers are the major products (83%) whereas the S,S-isomers are the minor (6%). In addition, the irreversible formation of two oxidation products, 3-(2-benzoylbenzoyl)quinolin-4(1H)-ones, and acridin-12(5H)-one derivatives was observed in the presence of air.

AB - Synthesis and characterization of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones is described. In addition to their potential biological activity, these compounds exhibit photoreversible photochromic properties in anaerobic conditions. Using the 1 and 2D NMR techniques we demonstrated that the coloration occurred owing to the formation of fluorescent 5a,6-dihydrobenzo[b]acridin-(5H)-ones. The photoreaction is stereoselective and the S,R-isomers are the major products (83%) whereas the S,S-isomers are the minor (6%). In addition, the irreversible formation of two oxidation products, 3-(2-benzoylbenzoyl)quinolin-4(1H)-ones, and acridin-12(5H)-one derivatives was observed in the presence of air.

KW - Acridine

KW - Fluorescence

KW - Hydrogen bonding

KW - Photochromism

KW - Quinolin-4(1H)-one

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DO - 10.1016/j.tet.2010.08.039

M3 - Article

AN - SCOPUS:77957203966

SN - 0040-4020

VL - 66

SP - 8291

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JO - Tetrahedron

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ER -

Synthesis and photochromism of a series of new 2-unsubstituted 3-(2-benzylbenzoyl)quinolin-4(1H)-ones

Abstract

Keywords

ASJC Scopus subject areas

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