Synthesis and photophysical properties of 2-aryl-5-carbonyl indolizines

Bertallo, Camila R.S.; Berlim, Leonardo S.; Olivier, Danilo S.; Arroio, Thais R.; Ito, Amando Siuiti; Clososki, Giuliano C.

doi:10.1016/j.dyepig.2021.109996

“…Indolizine and its derivatives possess broad range of biological activity towards many biological targets and therefore widely used in therapeutic applications [4]. In addition, electron‐rich indolizine scaffold is responsible for many interesting properties such as aromaticity, planarity, compatibility, polarity and fluorescence [5]. These qualities of indolizine derivatives make them essential part of dye‐sensitized solar cells (DSSC) [6] and organic light emitting devices (OLED) [7] known for their noticeable photo‐physical and fluorescent properties (Scheme 1).…”

Section: Methodsmentioning

confidence: 99%

Metal/catalyst/alkyne/alkene‐free one‐pot synthesis of indolizines from 2‐(pyridin‐2‐yl)acetate, DMF‐DMA and α‐halomethylenes

Lee

¹

,

Lee

²

,

Jeong

³

2023

Journal of Heterocyclic Chem

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We have described a simple and robust one‐pot synthesis of 1,3‐disubstitued‐indolizines from 2‐(pyridin‐2‐yl)acetate, DMF‐DMA and α‐halomethylenes without using metal/catalyst/alkyne/alkene. This protocol provides variety of indolizine analogs via in‐situ formed 3‐(dimethylamino)‐2‐(pyridin‐2‐yl)acrylate intermediate, undergoes N‐alkylation followed by Michael addition/cyclization. The gram scale synthesis of indolizine developed by this protocol does not require chromatographic purification. The post synthesis application of alkyne bearing indolizine provided triazole and a beta‐ketoester containing indolizine provided indolizine‐tethered pyrimidine heterocyclic system.

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The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

Antón-Cánovas

¹

,

Alonso

²

2022

Angewandte Chemie

1

0

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C-H bond formylation is the most immediate way to incorporate the versatile formyl group into (hetero)aromatics. However, the type of reagents and severe conditions involved in the classical formylation methods often curtail their application, especially in the presence of other functional groups. Herein, we present the Eschenmoser's salt, a commercially available (dimethylamino)methylating chemical, as a useful reagent for the C-H formylation of indolizines and other compounds. The method is straightforward and mild, furnishing indolizinecarbaldehydes in modest-to-good yields with exclusive and remote regioselectivity. Furthermore, these compounds can be easily transformed into pushpull dyes and are highly selective in the colorimetric detection of nitrite, a substance extensively employed as preservative in the food industry, the concentration of which is crucial to control to prevent harmful effects in living organisms. The assay is simple, allowing the naked-eye detection of nitrite in solution or on a cotton swab for a wide range of concentrations.

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The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

Antón-Cánovas

¹

,

Alonso

²

2022

View full text Add to dashboard Cite

C-H bond formylation is the most immediate way to incorporate the versatile formyl group into (hetero)aromatics. However, the type of reagents and severe conditions involved in the classical formylation methods often curtail their application, especially in the presence of other functional groups. Herein, we present the Eschenmoser's salt, a commercially available (dimethylamino)methylating chemical, as a useful reagent for the C-H formylation of indolizines and other compounds. The method is straightforward and mild, furnishing indolizinecarbaldehydes in modest-to-good yields with exclusive and remote regioselectivity. Furthermore, these compounds can be easily transformed into pushpull dyes and are highly selective in the colorimetric detection of nitrite, a substance extensively employed as preservative in the food industry, the concentration of which is crucial to control to prevent harmful effects in living organisms. The assay is simple, allowing the naked-eye detection of nitrite in solution or on a cotton swab for a wide range of concentrations.

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Synthesis and photophysical properties of 2-aryl-5-carbonyl indolizines

Cited by 12 publications

References 57 publications

Metal/catalyst/alkyne/alkene‐free one‐pot synthesis of indolizines from 2‐(pyridin‐2‐yl)acetate, DMF‐DMA and α‐halomethylenes

Metal/catalyst/alkyne/alkene‐free one‐pot synthesis of indolizines from 2‐(pyridin‐2‐yl)acetate, DMF‐DMA and α‐halomethylenes

The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

The Eschenmoser's Salt as a Formylation Agent for the Synthesis of Indolizinecarbaldehydes and Their Use for Colorimetric Nitrite Detection

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