The iodine-mediated highly regioselective synthesis of angular and linear naphthofuroquinones

Liu, Suyou; Li-jun, Long; Xie, Duoduo; Liu, Lijun; Ma, Da‐You

doi:10.1016/j.tetlet.2015.10.058

Cited by 9 publications

(5 citation statements)

References 32 publications

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“…These three compounds have already been published and all spectroscopical data are in accord with the literature. 13,17,18 We only observed the formation of olefin 3a with E-configuration. This configuration was confirmed by the two doublet signals in 1 H NMR spectrum with a coupling constant value of 16.7 Hz (J H,H olefin).…”

Section: Scheme 2 Synthesis Of Styrenes 5c-i Through Wittig Reactionsmentioning

confidence: 85%

“…HRMS: m/z [M + Na] + calcd for C 18 H 10 O 3 Na: 297.0522; found: 297.0528. Phenylnaphtho[1,2-b]furan-4,5-dione (8) 18 This compound was obtained as a side product from reaction between 4 and 5a; reddish-purple solid; mp 193-194 °C. 1 H NMR (400 MHz, CDCl 3 ): δ = 8.06 (d, J = 7.7 Hz, 1 H), 7.78 (d, J = 7.7 Hz, 1 H), 7.73 (dd, J = 7.0, 1.1 Hz, 2 H), 7.67 (td, J = 7.6, 1.2 Hz, 1 H), 7.49-7.42 (m, 3 H), 7.41-7.35 (m, 1 H), 7.01 (s, 1 H).…”

Section: -mentioning

confidence: 99%

“…C NMR (101 MHz, CDCl 3 ): δ = 171.08, 170. 14, 137.26, 135.22, 133.35, 127.23, 127.17, 126.19, 126.18, 125.64, 125.61, 119.78, 70.58, 70.54, 69.15, 69.11, 63.57, 63.54, 29.68 Phenylnaphtho[2,3-b]furan-4,9-dione (7) 18 This compound was obtained as a side product from the reaction between 4 and 5a; orange solid; mp 236-237 °C.…”

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confidence: 99%

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Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400

2017

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Styrenes were coupled with 3-iodolawsone in PEG-400 at 90 °C, leading stereoselectively to (E)-stilbene-quinone hybrids through Heck reactions. The best reaction conditions were found to be the use of NaOH (3 equiv) and 10 mol% of palladium acetate at 90 °C for 15 minutes. The chemical yields of the Heck reactions using styrenes with electron-withdrawing groups (65–98%) were greater than styrenes bearing electron-donating groups (7–32%) on the aromatic ring. In particular, the chemical yields of Heck reactions involving nitrostyrenes were the best ones observed.

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Section: Scheme 2 Synthesis Of Styrenes 5c-i Through Wittig Reactionsmentioning

confidence: 85%

Section: -mentioning

confidence: 99%

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Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400

2017

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“…Furthermore, naphtho[2,3‐ b ]furan‐4,9‐diones exhibit significant biological activity, such as anticancer, antitumor, antiproliferative, and trypanocidal activities, as well as activity against the growth of human keratinocyte . Consequently, the synthesis of naphtho[2,3‐ b ]furan‐4,9‐dione derivatives has attracted considerable attention in the past decades …”

Section: Introductionmentioning

confidence: 99%

NIS‐Induced Enone Difunctionalization for the Synthesis of Naphtho[2,3‐b]furan‐4,9‐diones

Liu

Zhu

et al. 2017

Eur J Org Chem

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An efficient synthesis of naphtho[2,3‐b]furan‐4,9‐diones has been developed by N‐iodosuccinimide (NIS)‐induced enone difunctionalization with 2‐hydroxy‐1,4‐naphthoquinones. This reaction involved sequential Michael addition, intramolecular oxidative cyclization and dehydrogenative aromatization to form new C–C and C–O bonds at the α and β positions of the enones. Various enones survived under the reaction conditions and the corresponding products were obtained in moderate‐to‐excellent yields.

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“…The wide spectrum of biological activities has attracted widespread interest in the field of medicinal chemistry; therefore, much effort has been focused on the synthetic methods of naphthofuroquinone derivatives. Over the past decades, base-catalyzed, bromine-mediated, different annulations − (such as thermal cyclization, photoaddition, oxidative cycloaddition, Diels–Alder cycloaddition/aromatization, oxidative cyclization/isomerization), one-pot cascades, and transition-metal-catalyzed syntheses of the naphthofuroquinone skeleton have been reported.…”

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confidence: 99%

Transition-Metal-Free One-Pot Synthesis of Naphthoquinonefuran Derivatives Through Sequential Nucleophilic Substitution–Nucleophilic Addition Reaction

Sun

Xie

et al. 2020

J. Org. Chem.

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A transition-metal-free route for tandem one-pot synthesis of naphthoquinonefuran derivatives from 2-hydroxynaphthoquinones has been developed. The sequentially accomplished process comprises an intermolecular alkynylation of sp2-carbon at the 3 position of 2-hydroxynaphthoquinones with arylethynyl bromides, followed by a base-promoted intramolecular nucleophilic annulation reaction. A broad range of functional groups is compatible with this reaction, and diverse naphtho[2,3-b]furan-4,9-diones can be obtained with good yields and excellent regioselectivity.

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The iodine-mediated highly regioselective synthesis of angular and linear naphthofuroquinones

Cited by 9 publications

References 32 publications

Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400

Synthesis of Stilbene-Quinone Hybrids through Heck Reactions in PEG-400

NIS‐Induced Enone Difunctionalization for the Synthesis of Naphtho[2,3‐b]furan‐4,9‐diones

Transition-Metal-Free One-Pot Synthesis of Naphthoquinonefuran Derivatives Through Sequential Nucleophilic Substitution–Nucleophilic Addition Reaction

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