Chemoselective Access to π‐Conjugated Heterocycles by Stille and Sonogashira Reactions on 2‐Substituted 4<i>H</i>‐Pyrido[<i>e</i>][1,3]oxazin‐4‐ones

Falher, Laetitia Le; Mumtaz, Amara; Diogo, Anthony Nina; Thorimbert, Serge; Botuha, Candice

doi:10.1002/ejoc.201601338

Cited by 4 publications

(7 citation statements)

References 38 publications

(14 reference statements)

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“…We hypothesized that expanded 𝜋-system will modify the energy levels and ICT characteristics of the newly obtained ESIPT compound and furnish bathochromic shifts in emission. [23] Absorption wavelength maxima of the 3-pyridyl ethynyl substituted triazole, 3Py-PyOHTr-10 [5] were observed in all solvent at 265 nm with a shoulder band around 320 nm, which is almost similar to the one obtained for its analogue PyOHTr-5. The presence of the 𝜋-extended conjugation on 3Py-PyOHTr-10 significantly affects fluorescence efficiency and emission characteristics.…”

Section: Resultssupporting

confidence: 68%

“…[4] shift, high photostability and dual fluorescence continue to be an active and competitive area of research for both fundamental and application point of view. We previously reported a rapid synthesis of hydroxypyridyl-1,2,4-oxadiazoles, -1,3,5-triazines and -1,2,4-triazoles, [5] and later synthetized two specimens of 𝜋-conjugated 2-hydroxypyridy-1,2,4-triazoles with promising fluorescent properties. [6] An unexpected extremely large Stokes shift over 10 000 cm −1 was observed in organic solvents which was suggested to be originated from an ESIPT between the hydroxyl group of the pyridol ring and the triazole moiety.…”

Section: Introductionmentioning

confidence: 99%

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3‐Hydroxypyridinyl‐Substituted‐1,2,4‐Triazoles as New ESIPT Based Fluorescent Dyes: Synthesis and Structure–Fluorescence Properties Correlations

Nina‐Diogo

Bertrand

Thorimbert

et al. 2023

Advanced Optical Materials

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This report presents the design, synthesis, and photophysical study of two new series of promising fluorescent trisubstituted triazoles, 3-hydroxypyridinyl substituted-1,2,4-triazoles (PyOHTr) and 2-pyridonyl substituted-1,2,4-triazoles (PyCOTr). An excited state intramolecular proton transfer (ESIPT) fluorescence mechanism is evidenced for PyOHTr molecules by ab initio theoretical calculations. These fluorescent dyes possess unique optical properties such as large Stokes shifts, dual emission, solvatochromism, solid-state emission and, for one of them, a white light emission, rendering them particularly attractive for future applications in both medicinal chemistry and materials science.

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Section: Resultssupporting

confidence: 68%

Section: Introductionmentioning

confidence: 99%

3‐Hydroxypyridinyl‐Substituted‐1,2,4‐Triazoles as New ESIPT Based Fluorescent Dyes: Synthesis and Structure–Fluorescence Properties Correlations

Nina‐Diogo

Bertrand

Thorimbert

et al. 2023

Advanced Optical Materials

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“…14 In the meantime, we have developed Pd(II)-catalyzed cross-coupling reactions on 2-substituted 4H-pyrido [1,3]oxazin-4-ones 3 to access polyfunctionalized precursors with extended π-conjugation for further applications as fluorescent materials. 15 Scheme 2 Transformation of 4H-pyrido [1,3]oxazin-4-ones into 2-hydroxypyridyl-1,2,4-oxadiazoles, -1,2,4-triazoles, and -1,3,5-triazines…”

Section: Short Review Syn Thesismentioning

confidence: 99%

“…38 The pyridinone 39 was obtained from 2-methoxypyridine 44 by a subsequent demethylation step using sodium iodide and TMSCl in boiling acetonitrile (Scheme 12). Thanks to 1 H, 13 C, and 15 N NMR experiments at ambient and low temperatures, all…”

Section: Scheme 11 Synthesis Of 5-methoxypyrazolo[34-c]pyridine By Tmentioning

confidence: 99%

‘Heteroaromatic Rings of the Future’: Exploration of Unconquered Chemical Space

Passador

Thorimbert

Botuha³

2018

Synthesis

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William Pitt and co-workers have created a virtual exploratory heterocyclic library ‘VEHICLe’ containing over 200 unconquered bicyclic heteroaromatic rings, synthetically feasible with potential medicinal interest. Since the publication of the 22 ‘heteroaromatic rings of the future’ by Pitt in 2009, 15 of them have been successfully synthesized as bicyclic or polycyclic forms and evaluated for applications in both biology and material science. This short review presents the critical synthesis associated with innovative synthetic methodologies of the synthetically conquered ring scaffolds from the list of 22 with a spotlight on the scientific contribution of this fascinating article for the expansion of the chemical diversity.1 Introduction2 Heteroaromatic Rings of the Future: The Synthetic challenge?2.1 4-Pyrido[1,3]oxazin-4-one-P1 2.2 Pyrrolo[2,1-b][1,3]oxazin-4-one-P4 2.3 Furo[2,1-e]pyridazin-4(1H)-one-P5 2.4 Isoxazolo[3,4-c]pyridin-7-one-P6 2.5 5H,6H-[1,2]Thiazolo[5,4-c]pyridin-5-one-P7 2.6 4H,5H-Furo[3,2-b]pyridin-5-one-P8 2.7 1H,5H,6H-Pyrazolo[3,4-c]pyridin-5-one-P9 2.8 Thieno[3,4-c]pyridazine-P10 2.9 Pyrrolo[1,2-c][1,2,3]triazine-P11 2.10 Thieno[3,4-a]oxazole-P12 2.11 2,4-Dihydropyrrolo[3,2-c]pyrazole-P13 2.12 Pyrazolo[1,5-b]isoxazole-P14 2.13 Imidazo[1,5-c]pyrimidin-3(2H)-one-P16 2.14 Cyclopenta[b][1,4]oxazin-5(4H)-one-P17 2.15 2,3-Dihydro-2,6-naphthyridin-3-one-P18 3 Conclusion

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“…Transitional metals and their complexes play a very important role during the formation of carbon-carbon bond. Palladium catalyzed cross-coupling reactions, [1,2] such as Suzuki-Miyaura reaction, [3,4] Sonogashira-coupling reaction, [5,6] Heck reaction, [7] Stille reaction, [8] Buchwald-Hartwig reaction [9] and Tsuji-Trost reaction, [10] are powerful methods for the creation of carbon-carbon bond, and have been widely used in the syntheses of pharmaceuticals, hydrocarbons, natural products, agrochemicals. [11] Suzuki-Miyaura reaction and Sonogashira coupling reactions can be achieved by using homogeneous palladium catalysts in the presence of a variety of auxiliary ligands, including amine-based, [12] phosphine-based, [13] bipyridinebased [14] and oxime-based [15] ligands.…”

mentioning

confidence: 99%