Indenopyrans – synthesis and photoluminescence properties

Diac, Andreea; Tepes, Ana-Maria; Soran, Albert; Grosu, Ion; Terec, Anamaria; Roncali, Jean; Bogdan, Elena

doi:10.3762/bjoc.12.81

Cited by 3 publications

(2 citation statements)

References 43 publications

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“…An interesting example that had been recently described is the involvement of diazolactones in an inverse electron-demand Diels–Alder reaction [13]. At the same time the synthesis of 3,4-dihydro-2 H -pyrans with a carboxamide group is a not sufficiently explored area.…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

Ievlev

Ершов

Belikov

et al. 2016

Beilstein J. Org. Chem.

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SummaryAn efficient diastereoselective approach for the synthesis of functionalized 3,4-dihydro-2H-pyran-4-carboxamides with variable frame was developed based on the reaction of available 4-oxoalkane-1,1,2,2-tetracarbonitriles (adducts of TCNE and ketones) with aldehydes in an acidic media. An unusual process of quasi hydrolysis of the cyano group was observed in the course of the described regio- and diastereoselective transformation.

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Section: Introductionmentioning

confidence: 99%

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

Ievlev

Ершов

Belikov

et al. 2016

Beilstein J. Org. Chem.

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“…Some of them have been reported to exhibit fluorescent properties and have been considered for the fabrication of OLEDs. 18 The same indenopyran subunit has been also found in different natural products which exhibit promising biological activities. For example, brazilin 1 isolated from sappanwood is used in traditional south-east Asian medicine.…”

mentioning

confidence: 98%

Access to Hexahydroindeno[2,1-c]pyran-Based Propellanes by a Domino Prins/Friedel–Crafts Cyclization

Nassar¹,

Fache²,

Pelotier³

et al. 2022

Synthesis

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Synthesis and Photophysical Properties of α‐Pyrone‐fused‐pyrido[3, 2,1‐jk]carbazolone Derivatives : DFT/TD‐DFT Insights

et al. 2018

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The present paper discloses an interesting microwave‐assisted solvent‐free protocol for the synthesis of thermally stable, highly fluorescent pyrano[2′, 3′:4,5]pyrido[3, 2,1‐jk]carbazole‐5,8‐diones in good to high yields with good quantum yields (Ø ≥ 0.70) through a [3+3] annulation reaction of aryl‐substituted Morita‐Baylis‐Hillman acetates with a 4‐hydroxy‐6H‐pyrido[3, 2,1‐jk]carbazol‐6‐one in the presence of Hünig's base. The solvatochromic properties of synthesized compounds have been determined which showed blue shifts in absorption and emission spectra with increasing the polarity of solvents. Similarly, the higher quantum yields were also observed in case of non‐polar solvents as compared to polar ones. Interestingly, the experimental results of photophysical properties were in good agreement with theoretical data obtained using B3LYP/6‐311G++(d,p) level of theory. Furthermore, the synthesized chromophoric scaffolds exhibited good thermal stability (342‐387 °C) and average fluorescence lifetime in the range of 2.011‐2.139 ns for 408 nm, 2.268‐2.277 ns for 428 nm.

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Indenopyrans – synthesis and photoluminescence properties

Cited by 3 publications

References 43 publications

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

Access to Hexahydroindeno[2,1-c]pyran-Based Propellanes by a Domino Prins/Friedel–Crafts Cyclization

Synthesis and Photophysical Properties of α‐Pyrone‐fused‐pyrido[3, 2,1‐jk]carbazolone Derivatives : DFT/TD‐DFT Insights

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