Photoinduced Regioselective Decarbonylative and Decarboxylative C–O Bond Functionalizations: Approach toward Chemoselective Scissions of Isatoic Anhydride and Unraveling the Enroutes through Control Experiments and DFT Studies DOI
Rahul Dev Mandal, Dwaipayan Das, Anindita Sarkar

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

Distinctive, green, innovative, and well-organized photoinduced (metal- or photocatalyst-free) regioselective decarbonylative decarboxylative C–O bond functionalization protocols to access aryl 2-aminobenzoates 2-substituted benzoxazinone derivatives in excellent yields have been devised. These are achieved through the chemoselective scission of isatoic anhydride with ketones, diaryliodonium triflate, nitroalkene, phthalazinone, phenol derivatives, which, turn, served as representative "electrophilic nucleophilic" coupling partners. Control experiments DFT calculations reveal that electrophilic radical-bearing partners specifically follow decarbonylation pathway, while nucleophilic conjugates facilitate decarboxylation process. Thus, devised methods represent fragmentation anhydride, which occurs due electronic nature Again, C–O/O–C formation is also a novel outcome this methodology. We green method for synthesizing 2-aminobenzoate-subtituted paracetamol route. A fluorescence quenching study indicates phenyl 2-aminobenzoate detects Fe(II) ions, exhibiting no reactivity toward various other metal ions. Additionally, transition-metal-catalyzed C–H vinyl sulfone was performed at ease significant yields, appreciated strategy developed by us.

Language: Английский

Innovative advancements in transition metal-catalyzed C(sp)-H bond activation of phthalazinone: Unlocking the gateway to diverse hybrid polyheterocyclic architectures DOI

Swarnali Ghosh,

Anindita Sarkar, Rahul Dev Mandal

et al.

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155618 - 155618

Published: April 1, 2025

Language: Английский

Citations

0
Harnessing the benzyne insertion consequence to enable π-extended pyrido-acridine and quinazolino-phenanthridine DOI

Swarnali Ghosh,

Dwaipayan Das, Rahul Dev Mandal

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(27), P. 5591 - 5602

Published: Jan. 1, 2024

Protocols have been devised for π-extended pyrido-acridines and quinazolino-phenanthridines, applying Rh( iii )- Pd( ii )-mediated catalytic courses. The parent compounds are realized from 2-aminobenzonitrile apposite benzyne precursor respectively.

Language: Английский

Citations

1
Skeletal Reorganization Emanated via the Course of Heterocyclic N1–N2 Bond Cleavage: Electrosynthetic Approach DOI
Saiful Islam, Dwaipayan Das,

Rahul Dev Mandal

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15686 - 15693

Published: Oct. 21, 2024

A unified method toward the synthesis of functionalized diazepines and quinazolines through reorganization molecular skeleton has been devised. The process is indulged by electrical energy via a domino N1–N2 bond cleavage followed concomitant ring closing, initiating from cinnolines indazoles as designed precursors. Additionally, an intermolecular homologation also established to synthesize densely dihydroquinazolines 2,3-diaryl-indazoles acetonitrile involving same electrochemical strategy.

Language: Английский

Citations

0
Photoinduced Regioselective Decarbonylative and Decarboxylative C–O Bond Functionalizations: Approach toward Chemoselective Scissions of Isatoic Anhydride and Unraveling the Enroutes through Control Experiments and DFT Studies DOI
Rahul Dev Mandal, Dwaipayan Das, Anindita Sarkar

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 5, 2024

Distinctive, green, innovative, and well-organized photoinduced (metal- or photocatalyst-free) regioselective decarbonylative decarboxylative C–O bond functionalization protocols to access aryl 2-aminobenzoates 2-substituted benzoxazinone derivatives in excellent yields have been devised. These are achieved through the chemoselective scission of isatoic anhydride with ketones, diaryliodonium triflate, nitroalkene, phthalazinone, phenol derivatives, which, turn, served as representative "electrophilic nucleophilic" coupling partners. Control experiments DFT calculations reveal that electrophilic radical-bearing partners specifically follow decarbonylation pathway, while nucleophilic conjugates facilitate decarboxylation process. Thus, devised methods represent fragmentation anhydride, which occurs due electronic nature Again, C–O/O–C formation is also a novel outcome this methodology. We green method for synthesizing 2-aminobenzoate-subtituted paracetamol route. A fluorescence quenching study indicates phenyl 2-aminobenzoate detects Fe(II) ions, exhibiting no reactivity toward various other metal ions. Additionally, transition-metal-catalyzed C–H vinyl sulfone was performed at ease significant yields, appreciated strategy developed by us.

Language: Английский

Citations

0