Details

Autor(en) / Beteiligte

• Obydennov, Dmitrii L
• Nigamatova, Diana I
• Shirinkin, Alexander S
• Melnikov, Oleg E
• Fedin, Vladislav V
• Usachev, Sergey A
• Simbirtseva, Alena E
• Kornev, Mikhail Y
• Sosnovskikh, Vyacheslav Y

Titel

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

Ist Teil von

• Molecules (Basel, Switzerland), 2022-12, Vol.27 (24)

Ort / Verlag

Switzerland

Erscheinungsjahr

2022

Quelle

MEDLINE

Beschreibungen/Notizen

• 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%).