Regioselective synthetic approach for key precursors of 6-arylbenzo[<i>c</i>]phenanthridin-10-ol derivatives: a useful compound for selective chromogenic recognition of fluoride

Yashmin, Sabina; Mondal, Santa; Das, Riyanka; Banerjee, Priyabrata; Khan, Abu T.

doi:10.1039/d2ob01260j

Cited by 5 publications

(2 citation statements)

References 43 publications

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“…This succinimide radical abstracts H· from 10th carbon of the phenolic compound ( 4 ) and helps for the bromination in the presence of Br· radical to form monobrominated intermediate A . Bromination at this particular benzylic carbon can be supported by our previous work . Next, intermediate A again undergoes radical bromination at another benzylic carbon (7th C of starting material 4 ) to give dibrominated intermediate B .…”

Section: Results and Discussionsupporting

confidence: 69%

“…Bromination at this particular benzylic carbon can be supported by our previous work. 12 It should be noted that the presence of the bromo functionality in the chromenophenanthridines can be benefitted in further synthetic organic conversions to accomplish new organic compounds through various cross coupling reactions such as Suzuki−Miyaura, Sonogashira cross-coupling reaction. As an example, compound 5a was used in Suzuki cross-coupling reaction with p-tolyl boronic acid to get the cross-coupled product 8a (Scheme 6).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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One-Step Synthesis of 7-Bromobenzo[c]chromeno[4,3,2-gh]phenanthridines through a Sequential Bromination/Cyclization/Aromatization Reaction Using N-Bromosuccinimide (NBS)

Yashmin,

Khan,

Akula

et al. 2023

J. Org. Chem.

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Herein, metal-and oxidant-free synthesis of 7bromobenzo [c]chromeno[4,3,2-gh]phenanthridines is reported using N-bromosuccinimide. Sequential regioselective bromination, intramolecular ring cyclization, and aromatization reactions occur in a single step through a successive radical-catalyzed pathway. The mechanistic pathway for the cyclization is supported by a DFT study. Selective bromination in the fully aromatic skeleton is accomplished without involving additional aromatic electrophilic ring bromination. As a synthetic application, the Suzuki coupling reaction of compound 5a with boronic acid is reported to get compound 8a. Aggregation-induced emission of one of the synthesized compounds (5h) is also investigated in THF/hexane solvent along with concentration-dependent emission spectroscopy.

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Section: Results and Discussionsupporting

confidence: 69%

Section: ■ Results and Discussionmentioning

confidence: 99%

One-Step Synthesis of 7-Bromobenzo[c]chromeno[4,3,2-gh]phenanthridines through a Sequential Bromination/Cyclization/Aromatization Reaction Using N-Bromosuccinimide (NBS)

Yashmin,

Khan,

Akula

et al. 2023

J. Org. Chem.

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Engineering a Two-in-one Ni(II)-azophenine switch: Intelligent Lab-on a-box device for decentralized recognition event

Das,

Banerjee

2023

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Synthesis of Pyranocoumarin through MCRs: Modulation of this Approach as a Function of Substituent Effect Forms the Furocoumarin and 4-Hydroxy-3-styryl Coumarin as a Function of Solvent Effect

Faraz,

Mehta,

Bharatam

et al. 2024

J. Org. Chem.

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The synthesis of pyranocoumarin is reported from 4-hydroxycoumarin, styrene oxide, and DMSO in the presence of p-TSA•H 2 O at 110 °C using a three-component reaction. Interestingly, a CH 2 moiety from DMSO gets inserted in this reaction to form the pyranocoumarin ring. The plausible mechanism for this interesting reaction was proposed and validated using quantum chemical methods. Interestingly, when the reactions were performed with 7-methoxy-4-hydroxycoumarin and styrene oxides, having an electron-withdrawing group, the reaction followed a two-component pathway, and furocoumarins were obtained in good yields. Switching the solvent from DMSO to CH 3 CN for the same reactants results in the exclusive formation of the novel monomeric product 4-hydroxy-3-styryl-2H-chromen-2-one (5) instead of the expected furocoumarins. Interestingly, one of the novel monomeric products, 4-hydroxy-3-styryl-2H-chromen-2-one, directly undergoes unexpected cyclization to provide a more interesting and complex tricyclic product. The salient features of the present strategy are its easy handling, commercial availability of starting material, metal-free synthesis, inexpensive catalysts, environmentally benign, and high atom economy.

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Regioselective synthetic approach for key precursors of 6-arylbenzo[c]phenanthridin-10-ol derivatives: a useful compound for selective chromogenic recognition of fluoride

Abstract: A regioselective synthetic strategy for 6-aryl-8,9-dihydro-benzo[c]phenanthridine-10(7H)-ones (4) is accomplished using a one-pot four-component reaction by fine-tuning of reaction temperature. DMSO is excellently used as a reactant-cum-solvent to introduce carbonyl functionality...

Cited by 5 publications

References 43 publications

One-Step Synthesis of 7-Bromobenzo[c]chromeno[4,3,2-gh]phenanthridines through a Sequential Bromination/Cyclization/Aromatization Reaction Using N-Bromosuccinimide (NBS)

One-Step Synthesis of 7-Bromobenzo[c]chromeno[4,3,2-gh]phenanthridines through a Sequential Bromination/Cyclization/Aromatization Reaction Using N-Bromosuccinimide (NBS)

Engineering a Two-in-one Ni(II)-azophenine switch: Intelligent Lab-on a-box device for decentralized recognition event

Synthesis of Pyranocoumarin through MCRs: Modulation of this Approach as a Function of Substituent Effect Forms the Furocoumarin and 4-Hydroxy-3-styryl Coumarin as a Function of Solvent Effect

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