DBU-Mediated Domino Annulation Reaction of 2-Amino-4H-chromen-4-ones and Aromatic Aldehydes for Synthesis of Polysubstituted 3-Hydroxy-5H-chromeno[2,3-b]pyridinones

Li, Haiwen; Xin, Junhu; Xue, Yuhang; Wang, Cunde

doi:10.1021/acs.joc.2c01152

Cited by 9 publications

References 51 publications

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HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones

Xiong

Zhang

et al. 2023

Adv Synth Catal

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Hexafluoroisopropanol (HFIP) has been extensively applied in organic synthesis as a versatile reaction media. However, the application of HFIP as an catalyst in organic synthesis has been rarely studied. Presented here, is the example of HFIP‐catalyzed Mannich‐type reaction between quinoxalin‐2(1H)‐ones and difluoroenoxysilanes. The developed protocol tolerates various substituents under mild reaction conditions, providing a divergent approach to the construction of difluoro‐substituted 3,4‐dihydroquinoxalin‐2(1H)‐ones and monofluoroquinoxalin‐2(1H)‐ones in 51–92% yields.

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HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones

Xiong

Zhang

et al. 2023

Adv Synth Catal

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Access to 2‐Sulfonyl‐4‐arylphenols and 2,6‐Bis‐sulfonyl 5‐Aryl‐4‐arylidene‐2‐cyclohexenones via Metal Triflates‐Catalyzed Domino Cyclocondensation of 1,3‐Bis‐sulfonylacetones and 3‐Arylacroleins

Chang,

Hsueh

2023

Adv Synth Catal

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Herein, metal triflates–catalyzed one‐pot domino cyclocondensation of 1,3‐bis‐sulfonylacetones and 3‐arylacroleins via (3+3) or (3+2+1) annulation has been proposed to construct diversified 2‐sulfonyl‐4‐arylphenols and 2,6‐bis‐sulfonyl 5‐aryl‐4‐arylidene‐2‐cyclohexenones. In this effective reaction, C−C and C=C bonds are formed via a cascade process and 3‐arylacrolein acts as a C3 and C1 synthon during the formation of a six‐membered ring system under mild conditions. A plausible mechanism has been proposed and discussed.

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Synthesis of Chromeno[2,3‐b]quinoline derivatives via ZnCl₂‐Mediated three‐component reaction of 2‐Aminochromenones, benzaldehydes and Cyclohexane‐1,3‐dione

Gan

Zhou

Shen³

et al. 2023

Journal of Heterocyclic Chem

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A novel ZnCl 2 -promoted three-component reaction strategy for the synthesis of hexahydrochromeno [2,3-b]quinoline derivatives via the Aldol condensation/Michael addition/cycloaddition/dehydration cascade reaction of 2-amino-4H-chromen-4-ones, aromatic aldehydes, and cyclohexane-1,3-dione was investigated. This procedure is environmentally friendly, highly efficient, and has a broad scope. The structures of the products obtained were determined based on x-ray diffraction studies.

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DBU-Mediated Domino Annulation Reaction of 2-Amino-4H-chromen-4-ones and Aromatic Aldehydes for Synthesis of Polysubstituted 3-Hydroxy-5H-chromeno[2,3-b]pyridinones

Cited by 9 publications

References 51 publications

HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones

HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones

Access to 2‐Sulfonyl‐4‐arylphenols and 2,6‐Bis‐sulfonyl 5‐Aryl‐4‐arylidene‐2‐cyclohexenones via Metal Triflates‐Catalyzed Domino Cyclocondensation of 1,3‐Bis‐sulfonylacetones and 3‐Arylacroleins

Synthesis of Chromeno[2,3‐b]quinoline derivatives via ZnCl₂‐Mediated three‐component reaction of 2‐Aminochromenones, benzaldehydes and Cyclohexane‐1,3‐dione

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DBU-Mediated Domino Annulation Reaction of 2-Amino-4H-chromen-4-ones and Aromatic Aldehydes for Synthesis of Polysubstituted 3-Hydroxy-5H-chromeno[2,3-b]pyridinones

Cited by 9 publications

References 51 publications

HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones

HFIP‐Catalyzed Mannich Reaction: Divergent Synthesis of Difluoro‐Substituted 3,4‐Dihydroquinoxalin‐2(1H)‐ones and Monofluoroquinoxalin‐2(1H)‐ones

Access to 2‐Sulfonyl‐4‐arylphenols and 2,6‐Bis‐sulfonyl 5‐Aryl‐4‐arylidene‐2‐cyclohexenones via Metal Triflates‐Catalyzed Domino Cyclocondensation of 1,3‐Bis‐sulfonylacetones and 3‐Arylacroleins

Synthesis of Chromeno[2,3‐b]quinoline derivatives via ZnCl2‐Mediated three‐component reaction of 2‐Aminochromenones, benzaldehydes and Cyclohexane‐1,3‐dione

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Synthesis of Chromeno[2,3‐b]quinoline derivatives via ZnCl₂‐Mediated three‐component reaction of 2‐Aminochromenones, benzaldehydes and Cyclohexane‐1,3‐dione