Regioselective Annulation of Unsymmetrical 1,2‐Phenylenebis(diaryl/diheteroarylmethanol): A Facile Synthesis of Anthracene, Tetracene, and Naphtho[<i>b</i>]thiophene Analogues

Sivasakthikumaran, Ramakrishnan; Rafiq, Settu Muhammad; Sankar, Elumalai; Clement, J. Arul; Mohanakrishnan, Arasambattu K.

doi:10.1002/ejoc.201501087

Cited by 13 publications

(9 citation statements)

References 97 publications

(44 reference statements)

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“…Given the importance of the chroman and tetrahydrofuran motifs, in the past decade, many strategies for accessing these structures have been developed . However, most of these strategies demand multiple steps that are conducted under different reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl₃/Et₃SiH System by Switching the Solvent

Jia

Liu

et al. 2019

J. Org. Chem.

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An efficient one-pot synthesis of O-heterocycles or aryl ketones has been achieved using Et3SiH in the presence of InCl3 via a sequential ionic hydrogenation reaction by switching the solvent. This methodology can be used to construct C–O bonds and to prepare conjugate reduction products, including chromans, tetrahydrofurans, tetrahydropyrans, dihydroisobenzofurans, dihydrochalcones, and 1,4-diones in a facile manner. In addition, a novel plausible mechanism involving a conjugate reduction and a tandem reductive cyclization was verified by experimental investigations.

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Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl₃/Et₃SiH System by Switching the Solvent

Jia

Liu

et al. 2019

J. Org. Chem.

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“…In a related approach, in 2015, Mohanakrishnan and his group reported the synthesis of anthracene derivatives and other annulated products via the regioselective cyclization of asymmetric 1,2-diarylmethine diol 83b by using a HBr/AcOH system ( Scheme 20 ) [ 54 ]. They obtained substituted anthracene derivatives in very good yields (71–94%) and representative examples included 84f – k [ 54 ]. By using both methodologies, the authors obtained substituted benzo[ a ]anthracenes from compounds 83 .…”

Section: Reviewmentioning

confidence: 99%

“…Mohanakrishnan's group has contributed with numerous methodologies for the synthesis of anthracene derivatives, mainly methodologies involving Lewis acid-mediated intramolecular cyclizations. For example, in 2012 they reported an annulation protocol to synthesize anthracene, tetracene, and In a related approach, in 2015, Mohanakrishnan and his group reported the synthesis of anthracene derivatives and other annulated products via the regioselective cyclization of asymmetric 1,2-diarylmethine diol 83b by using a HBr/AcOH system (Scheme 20) [54]. They obtained substituted anthracene deriva-Scheme 20: Lewis acid-mediated regioselective cyclization of asymmetric diarylmethine dipivalates and diarylmethine diols.…”

Section: Intramolecular Cyclizationmentioning

confidence: 99%

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Recent advances in the syntheses of anthracene derivatives

Baviera

Donate

2021

Beilstein J. Org. Chem.

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Anthracene and anthracene derivatives have been extensively studied over the years because of their interesting photophysical, photochemical, and biological properties. They are currently the subject of research in several areas, which investigate their use in the biological field and their application in OLEDs, OFETs, polymeric materials, solar cells, and many other organic materials. Their synthesis remains challenging, but some important preparative methods have been reported, especially in the last decade. This review presents an update of the recent strategies that have been employed to prepare anthracene derivatives. It encompasses papers published over the last twelve years (2008–2020) and focuses on direct and indirect methods to construct anthracene and anthraquinone frameworks.

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“…The 2,7-dibromocarbazolylphthalide 14h similarly afforded the naphthocarbazole 15h in 88% yield (entry 7). Reductive cyclization of the 2,3-bis(hexyloxy)naphthalenylphthalide 14i 26 gave benzo[a]anthracene-2,3-diol (15i), with cleavage of the hexyloxy ether units (entry 8).…”

Section: Letter Syn Lettmentioning

confidence: 99%

Synthesis of Annulated Arenes and Heteroarenes by Hydriodic Acid and Red Phosphorus Mediated Reductive Cyclization of 2-(Hetero)aroylbenzoic Acids or 3-(Hetero)arylphthalides

Rafiq

Mohanakrishnan

2016

Synlett

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All melting points were uncorrected. Solvents were dried by standard procedures. The progression of all the reaction was monitored by TLC using hexanes/ethyl acetate mixture as eluent. Column chromatography was carried out on Silica gel (230-400 mesh, Merck) by using increasing polarity. 1 H, 13 C and Dept-135 spectra were recorded in CDCl 3 , DMSO-d 6 , and acetone-d 6 using TMS as an internal standard on a 300 MHz spectrometer at room temperature. Chemical shift values were quoted in parts per million (ppm) and coupling constants (J) were quoted in hertz (Hz). Commercially available 57% hydriodic acid purchased from Avra was used in the reaction (CAS number-10034-85-2). The required keto-acids 6, 1a 10, 1a pthalides 9, 1b 13, 1b 14a-g, 1b-d 14h, 1b 14i, 1d 16-b, 1b-c 19a-b, 1c-d 22a-c, 1b-d bis-phthalides 24a-b, 1b 26a-c, 1b 26d-f, 2 26g-h 2 and keto-acids 28a-h 1a, 2 were prepared adopting the reported procedures. General procedure: Reductive cyclization of keto-acid 6 using HI/P: 5-Hexyl-5H-naphtho[2,3-c]carbazole 7 and naphtho[2,3-b]carbazole 8 To a solution of keto-acid 6 (0.4 g, 1.0 mmol) in glacial acetic acid (30 mL), 57% HI (2.49 mL, 20 mmol) and red phosphorus (0.37 g, 12 mmol) were added and refluxed for 24 h. The red phosphorus was then filtered off. To the filtrate, ice-water (100 mL) was added and the precipitated solid was filtered and washed successively with aq. sodium thiosulphate (30 mL) followed by water (60 mL) and air dried. The crude product was purified by column chromatography (silica gel, hexane) to afford 5-hexyl-naphtho[2,3-c]carbazole 7 (0.144 g, 41%). Further elution of the column (silica gel, 1% EA in hexane) furnished 5-hexyl-5H-naphtho[2,3b]carbazole 8 (0.127 g, 36%) as a yellow solid. 7: mp 104-106 o C (Lit. 4c 104 o C). 1 H-NMR (300

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Regioselective Annulation of Unsymmetrical 1,2‐Phenylenebis(diaryl/diheteroarylmethanol): A Facile Synthesis of Anthracene, Tetracene, and Naphtho[b]thiophene Analogues

Cited by 13 publications

References 97 publications

One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl₃/Et₃SiH System by Switching the Solvent

One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl₃/Et₃SiH System by Switching the Solvent

Recent advances in the syntheses of anthracene derivatives

Synthesis of Annulated Arenes and Heteroarenes by Hydriodic Acid and Red Phosphorus Mediated Reductive Cyclization of 2-(Hetero)aroylbenzoic Acids or 3-(Hetero)arylphthalides

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Regioselective Annulation of Unsymmetrical 1,2‐Phenylenebis(diaryl/diheteroarylmethanol): A Facile Synthesis of Anthracene, Tetracene, and Naphtho[b]thiophene Analogues

Cited by 13 publications

References 97 publications

One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl3/Et3SiH System by Switching the Solvent

One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl3/Et3SiH System by Switching the Solvent

Recent advances in the syntheses of anthracene derivatives

Synthesis of Annulated Arenes and Heteroarenes by Hydriodic Acid and Red Phosphorus Mediated Reductive Cyclization of 2-(Hetero)aroylbenzoic Acids or 3-(Hetero)arylphthalides

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One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl₃/Et₃SiH System by Switching the Solvent

One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl₃/Et₃SiH System by Switching the Solvent