Metal template ortho-acylation of phenols; A new general approach to anthracyclinones

Sartori, Giovanni; Casnati, Giuseppe; Bigi, Franca; Robles, Pasquale

doi:10.1016/s0040-4039(01)81035-2

Cited by 29 publications

(7 citation statements)

References 11 publications

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“…PTF was conveniently synthesized by a one-step method according to the literature. [11] Then, carbazolyl groups were introduced to produce PTCz via the Ullmann reaction (Scheme S1, Supporting Information). All compounds were well characterized by 1 H NMR, 13 C NMR, mass spectrometry, elemental analysis, and single crystal diffractometry.…”

Section: Photophysical Properties Of Ptczmentioning

confidence: 99%

Luminous Butterflies: Rational Molecular Design to Optimize Crystal Packing for Dramatically Enhanced Room‐Temperature Phosphorescence

Ruan

Liao

Dang

et al. 2021

Advanced Optical Materials

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bioimaging, organic light-emitting diodes, and anticounterfeiting technology. [1] However, p-RTP systems are usually restricted to inorganic materials based on transition metal complexes, wherein the heavy metal facilitates the spin-orbital coupling (SOC) in favor of enhancing intersystem crossing (ISC). [2] As promising alternatives, pure organic p-RTP luminogens possess advantages such as low cost, rich species, excellent processability, fantastic flexibility, and good biocompatibility. However, on account of their forbidden nature and the susceptibility of triplet excitons, they are difficult to fabricate. [3] A general strategy to obtain organic p-RTP materials is to enhance ISC from the singlet state to triplet state. Thus, lots of the reported organic p-RTP materials are carbonyl based donor (D)-acceptor (A) molecules, which can effectively enhance the ISC process. [4,5] Thanks to the great efforts of scientists, various derivatives had been synthesized, and the molecular structures and packing showed important impact on their room-temperature phosphorescence (RTP) performance. However, compared to the traditional carbonyl, the exploitation of new building block is relatively backward, hindering the development of new molecular design concepts. Thus, it is very important to expand the organic p-RTP family for the further exploring of the inherent mechanism and the understanding of the molecular structure-packing-performance relationship. [6] Phthalide (PT) unit consisting of a benzene ring fused with a γ-lactone, represents privileged structural subunits in molecules of medicinal chemistry. PT framework plays a vital role as a building block in the synthesis of many natural products and pharmaceutical drugs. And PT-containing drugs have gained worldwide popularity because of the wide range of pharmacophore activities, such as anti-platelet accumulation, anti-angina, and central nervous system modulation (Chart S1, Supporting Information). [7] In addition, compared to simple CO, PT unit offered additional O atom with lone pair electrons and benzene ring with π orbitals, which could conduce to n-π* transitions and intersystem crossing. So, to further enrich the species and functions of organic p-RTP molecules, especially to excavate their potential applications, in this work, PT unit was selected as a new building block to construct efficient and robust pure organic p-RTP molecular system.In general, the properties of organic molecules for persistent room-temperature phosphorescence (p-RTP) rely heavily on the molecular packing in aggregated state, and the molecular packing is highly related to the structure and electronic properties of molecules. Thus, through rational design of molecules, it is possible to control the packing and hence the properties of p-RTP molecules. In this work, traditional CO is replaced by phthalide (PT) unit to achieve desired molecular packing with strong intermolecular interactions. Butterflylike molecules are successfully synthesized, which show bright mechanoluminescence (M...

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Section: Photophysical Properties Of Ptczmentioning

confidence: 99%

Luminous Butterflies: Rational Molecular Design to Optimize Crystal Packing for Dramatically Enhanced Room‐Temperature Phosphorescence

Ruan

Liao

Dang

et al. 2021

Advanced Optical Materials

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“…[88][89][90][91] A better strategy constitutes the synthesis of substituted benzoylated pyridines 118 or 119 and subsequent ring closure. The synthesis of pyridines 118 and 119 can be performed via initial lithiation of pyridines and subsequent reaction with suitable arenes, 90,92,93 or alternatively via lithiated arenes which can react with isonicotinic esters 94 or activated pyridines.…”

Section: Synthetic Approaches Towards 2-azaanthraquinonesmentioning

confidence: 99%

“…In view of the physiological importance of 2-aza-anthraquinones, as outlined above, considerable efforts have been devoted to establish efficient synthetic strategies of these compounds. To date, three major synthetic pathways have been developed (Scheme 20): (i) via cycloaddition reactions of suitable dienes to isoquinoline-5,8dione or naphthoquinone derivatives 115 and 116 [81][82][83][84][85][86][87] (ii) via initial acylation of pyridines or substituted arenes followed by an intramolecular condensation/cyclization of intermediates 118 or 119 [88][89][90][91][92][93][94][95][96][97] and (iii) via construction of the heterocyclic ring starting from substituted naphthoquinones 120 or 121 [cf. the biomimetic construction of bostrycoidin starting from fusarubin ( 96)].…”

Section: Synthetic Approaches Towards 2-azaanthraquinonesmentioning

confidence: 99%

A Survey of Synthetic Routes towards the Pyranonaphthoquinone Antibiotic Pentalongin and Syntheses of the Corresponding Nitrogen Derivatives

Claessens¹,

Verniest²,

Jacobs³

et al. 2007

Synlett

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A survey through the synthetic possibilities of pentalongin and its derivatives is presented. Pentalongin is the parent compound in the 3,4-dehydropyranonaphthoquinone series and is the active principle of the medicinal plant Pentas longiflora. Attention is paid to eight approaches towards these 3,4-dehydropyranonaphthoquinones. Synthetic methodologies for the corresponding nitrogen analogues are described, focusing on several natural products.

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“…As mentioned above, anthraquinone derivatives are very attractive compounds and have drawn much attention due to interest in the synthesis of their analogues; for example, cyclobutenedione chemistry, 6 direct ortho-metalation, 7 Hauser annulation, 8 direct arene oxidation, 9 and FriedelCrafts reaction 10 have been reported.…”

mentioning

confidence: 99%

“…Even recently, unknown anthraquinone derivatives have been isolated 4 and newly designed anthraquinone derivatives have also been synthesized as biologically active agents. 5 As mentioned above, anthraquinone derivatives are very attractive compounds and have drawn much attention due to interest in the synthesis of their analogues; for example, cyclobutenedione chemistry, 6 direct ortho-metalation, 7 Hauser annulation, 8 direct arene oxidation, 9 and Friedel-Crafts reaction 10 have been reported.…”

mentioning

confidence: 99%

Synthesis of Anthraquinone Derivatives: Tandem Diels-Alder-Decarboxylation-Oxidation Reaction of 3-Hydroxy-2-pyrone with 1,4-Naphthoquinone

Komiyama¹,

Takaguchi²,

Tsuboi³

2006

Synlett

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Metal template ortho-acylation of phenols; A new general approach to anthracyclinones

Cited by 29 publications

References 11 publications

Luminous Butterflies: Rational Molecular Design to Optimize Crystal Packing for Dramatically Enhanced Room‐Temperature Phosphorescence

Luminous Butterflies: Rational Molecular Design to Optimize Crystal Packing for Dramatically Enhanced Room‐Temperature Phosphorescence

A Survey of Synthetic Routes towards the Pyranonaphthoquinone Antibiotic Pentalongin and Syntheses of the Corresponding Nitrogen Derivatives

Synthesis of Anthraquinone Derivatives: Tandem Diels-Alder-Decarboxylation-Oxidation Reaction of 3-Hydroxy-2-pyrone with 1,4-Naphthoquinone

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Metal template ortho-acylation of phenols; A new general approach to anthracyclinones

Cited by 29 publications

References 11 publications

Luminous Butterflies: Rational Molecular Design to Optimize Crystal Packing for Dramatically Enhanced Room‐Temperature Phosphorescence

Luminous Butterflies: Rational Molecular Design to Optimize Crystal Packing for Dramatically Enhanced Room‐Temperature Phosphorescence

A Survey of Synthetic Routes towards the Pyranonaphthoquinone Antibiotic Pentalongin and Syntheses of the Corresponding Nitrogen Derivatives

Synthesis of Anthraquinone Derivatives: Tandem Diels-Alder-Decarboxyl­ation-Oxidation Reaction of 3-Hydroxy-2-pyrone with 1,4-Naphthoquinone

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Synthesis of Anthraquinone Derivatives: Tandem Diels-Alder-Decarboxylation-Oxidation Reaction of 3-Hydroxy-2-pyrone with 1,4-Naphthoquinone