Standard

2-(2-(Dimethylamino)vinyl)-4H-pyran-4-ones as Novel and Convenient Building-Blocks for the Synthesis of Conjugated 4-Pyrone Derivatives. / Obydennov, Dmitrii L.; Nigamatova, Diana I.; Shirinkin, Alexander S. et al.
In: Molecules, Vol. 27, No. 24, 8996, 13.12.2022.

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

Harvard

Obydennov, DL, Nigamatova, DI, Shirinkin, AS, Melnikov, OE, Fedin, VV, Usachev, SA, Simbirtseva, AE, Kornev, MY & Sosnovskikh, VY 2022, '2-(2-(Dimethylamino)vinyl)-4H-pyran-4-ones as Novel and Convenient Building-Blocks for the Synthesis of Conjugated 4-Pyrone Derivatives', Molecules, vol. 27, no. 24, 8996. https://doi.org/10.3390/molecules27248996

APA

Obydennov, D. L., Nigamatova, D. I., Shirinkin, A. S., Melnikov, O. E., Fedin, V. V., Usachev, S. A., Simbirtseva, A. E., Kornev, M. Y., & Sosnovskikh, V. Y. (2022). 2-(2-(Dimethylamino)vinyl)-4H-pyran-4-ones as Novel and Convenient Building-Blocks for the Synthesis of Conjugated 4-Pyrone Derivatives. Molecules, 27(24), [8996]. https://doi.org/10.3390/molecules27248996

Vancouver

Obydennov DL, Nigamatova DI, Shirinkin AS, Melnikov OE, Fedin VV, Usachev SA et al. 2-(2-(Dimethylamino)vinyl)-4H-pyran-4-ones as Novel and Convenient Building-Blocks for the Synthesis of Conjugated 4-Pyrone Derivatives. Molecules. 2022 Dec 13;27(24):8996. doi: 10.3390/molecules27248996

Author

Obydennov, Dmitrii L. ; Nigamatova, Diana I. ; Shirinkin, Alexander S. et al. / 2-(2-(Dimethylamino)vinyl)-4H-pyran-4-ones as Novel and Convenient Building-Blocks for the Synthesis of Conjugated 4-Pyrone Derivatives. In: Molecules. 2022 ; Vol. 27, No. 24.

BibTeX

@article{f248f9f369c84b18b811bcc6d5115255,
title = "2-(2-(Dimethylamino)vinyl)-4H-pyran-4-ones as Novel and Convenient Building-Blocks for the Synthesis of Conjugated 4-Pyrone Derivatives",
abstract = "A straightforward approach for the construction of the new class of conjugated pyrans based on enamination of 2-methyl-4-pyrones with DMF-DMA was developed. 2-(2-(Dimethylamino)vinyl)-4-pyrones are highly reactive substrates that undergo 1,6-conjugate addition/elimination or 1,3-dipolar cycloaddition/elimination followed by substitution of the dimethylamino group without ring opening. This strategy includes selective transformations leading to conjugated and isoxazolyl-substituted 4-pyrone structures. The photophysical properties of the prepared 4-pyrones were determined in view of further design of novel merocyanine fluorophores. A solvatochromism was found for enamino-substituted 4-pyrones accompanied by a strong increase in fluorescence intensity in alcohols. The prepared conjugated structures demonstrated valuable photophysical properties, such as a large Stokes shift (up to 204 nm) and a good quantum yield (up to 28%). ",
author = "Obydennov, {Dmitrii L.} and Nigamatova, {Diana I.} and Shirinkin, {Alexander S.} and Melnikov, {Oleg E.} and Fedin, {Vladislav V.} and Usachev, {Sergey A.} and Simbirtseva, {Alena E.} and Kornev, {Mikhail Y.} and Sosnovskikh, {Vyacheslav Y.}",
note = "This research was funded by the Russian Science Foundation, grant number 18-13-00186 (https://rscf.ru/project/18-13-00186/ (accessed on 12 December 2022)).",
year = "2022",
month = dec,
day = "13",
doi = "10.3390/molecules27248996",
language = "English",
volume = "27",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "24",

}

RIS

TY - JOUR

T1 - 2-(2-(Dimethylamino)vinyl)-4H-pyran-4-ones as Novel and Convenient Building-Blocks for the Synthesis of Conjugated 4-Pyrone Derivatives

AU - Obydennov, Dmitrii L.

AU - Nigamatova, Diana I.

AU - Shirinkin, Alexander S.

AU - Melnikov, Oleg E.

AU - Fedin, Vladislav V.

AU - Usachev, Sergey A.

AU - Simbirtseva, Alena E.

AU - Kornev, Mikhail Y.

AU - Sosnovskikh, Vyacheslav Y.

N1 - This research was funded by the Russian Science Foundation, grant number 18-13-00186 (https://rscf.ru/project/18-13-00186/ (accessed on 12 December 2022)).

PY - 2022/12/13

Y1 - 2022/12/13

N2 - A straightforward approach for the construction of the new class of conjugated pyrans based on enamination of 2-methyl-4-pyrones with DMF-DMA was developed. 2-(2-(Dimethylamino)vinyl)-4-pyrones are highly reactive substrates that undergo 1,6-conjugate addition/elimination or 1,3-dipolar cycloaddition/elimination followed by substitution of the dimethylamino group without ring opening. This strategy includes selective transformations leading to conjugated and isoxazolyl-substituted 4-pyrone structures. The photophysical properties of the prepared 4-pyrones were determined in view of further design of novel merocyanine fluorophores. A solvatochromism was found for enamino-substituted 4-pyrones accompanied by a strong increase in fluorescence intensity in alcohols. The prepared conjugated structures demonstrated valuable photophysical properties, such as a large Stokes shift (up to 204 nm) and a good quantum yield (up to 28%).

AB - A straightforward approach for the construction of the new class of conjugated pyrans based on enamination of 2-methyl-4-pyrones with DMF-DMA was developed. 2-(2-(Dimethylamino)vinyl)-4-pyrones are highly reactive substrates that undergo 1,6-conjugate addition/elimination or 1,3-dipolar cycloaddition/elimination followed by substitution of the dimethylamino group without ring opening. This strategy includes selective transformations leading to conjugated and isoxazolyl-substituted 4-pyrone structures. The photophysical properties of the prepared 4-pyrones were determined in view of further design of novel merocyanine fluorophores. A solvatochromism was found for enamino-substituted 4-pyrones accompanied by a strong increase in fluorescence intensity in alcohols. The prepared conjugated structures demonstrated valuable photophysical properties, such as a large Stokes shift (up to 204 nm) and a good quantum yield (up to 28%).

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85144489390

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=000904269600001

U2 - 10.3390/molecules27248996

DO - 10.3390/molecules27248996

M3 - Article

VL - 27

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 24

M1 - 8996

ER -

ID: 33229831