An Efficient Synthetic Protocol for Quinoxalinones, Benzoxazinones, and Benzothiazinones from 2‐Oxo‐2‐aryl‐acetyl Bromide Precursors

Nagaraj, Muthupandi; S, Sathiyamoorthy; Boominathan, Muthusamy; Muthusubramanian, Shanmugam; Bhuvanesh, Nattamai

doi:10.1002/jhet.1557

Cited by 19 publications

(8 citation statements)

References 28 publications

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“…Based on our experimental results described above and the literatures, 12,13 functionalization are achieved in one pot under the mild reaction conditions. This oxidation cyclization reaction provides an environmentally friendly protocol to heterocyclic compounds.…”

Section: Resultsmentioning

confidence: 98%

“…The title compound was prepared according to the general procedure and purified by column chromatography on silica gel and eluted with petroleum ether/EtOAc (10:1) to afford the desired product in 80%, faint yellow solid, mp 129-131 o C. 1 [1,4]thiazin-2-one (3h) 12 The title compound was prepared according to the general procedure and purified by column chromatography on silica gel and eluted with petroleum ether/EtOAc (10:1) to afford the desired product in 80%, white solid, mp 171-173 o C. 1…”

Section: -(4-iodophenyl)-2h-benzo[b][14]thiazin-2-one (3g)mentioning

confidence: 99%

“…11 Recently, a new procedure was reported to gain quinoxalinone, benzoxazinone, and benzothiazinone heterocyclic compounds through two steps, first 2-oxo-2-arylacetyl bromides were synthesized by selenium dioxide oxidation of α-bromoketones, then 2-oxo-2-arylacetyl bromides react with aryl-1,2-diamines, 2-aminophenol or 2-aminothiophenol to give corresponding heterocyclic compounds. 12 Although various methods have been reported for constructing the heterocycles, metal oxides, microwave irradiation, and peroxide were needed and accompanied complex operations.…”

Section: Introductionmentioning

confidence: 99%

“…H NMR (400 MHz, CDCl3): δ 8.93 (d, J = 8.0 Hz, 2H), 8.27 (d, J = 7.6 Hz, 1H), 8.03 (q, J = 7.2 Hz, 1H), 7.57-7.62 (m, 2H), 7.79 (d, J = 8.0 Hz, 2H); 13 C NMR (100 MHz, CDCl3): δ 184.4, 166.9, 153.9, 137.2, 133.8, 132.9, 132.0, 129.7, 127.9, 127.2, 125.9, 122.4. MS (EI), m/z = 284.3-(Naphthalen-1-yl)-2H-benzo[b][1,4]thiazin-2-one (3i)12 The title compound was prepared according to the general procedure and purified by column chromatography on silica gel and eluted with petroleum ether/EtOAc (10:1) to afford the desired product in 79%, white solid, mp 162-165 o C 1. H NMR (400 MHz, CDCl3): δ 9.26 (s, J = 8.0 Hz, 1H), 8.31-8.36 (m, 3H), 8.19 (d, J = 8.0 Hz, 1H), 8.12 (d, J = 8.0 Hz, 1H), 8.06 (d, J = 8.0 Hz, 1H), 7.68-7.76 (m, 4H); NMR (100 MHz, CDCl3): δ 185.3, 167.3, 153.8, 136.7, 135.8, 134.1, 132.3, 130.5, 129.9, 128.8, 128.6, 128.2, 127.9, 127.7, 126.0, 123.4.…”

mentioning

confidence: 99%

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Metal-Free sp3 C-H Bond Oxidation and Functionalization of α-Bromoketones to Quinoxalinone, Benzoxazinone, and Benzothiazinone Heterocyclic Compounds

Chen¹,

Guo²,

Tian-long³

et al. 2021

HETEROCYCLES

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Section: Resultsmentioning

confidence: 98%

Section: -(4-iodophenyl)-2h-benzo[b][14]thiazin-2-one (3g)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Metal-Free sp3 C-H Bond Oxidation and Functionalization of α-Bromoketones to Quinoxalinone, Benzoxazinone, and Benzothiazinone Heterocyclic Compounds

Chen¹,

Guo²,

Tian-long³

et al. 2021

HETEROCYCLES

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“…Nagaraj et al. reported a useful protocol for the synthesis of quinoxalinones from 2‐oxo‐2‐aryl‐acetyl bromide precursors . Mtiraoui et al.…”

Section: Introductionmentioning

confidence: 99%

Ready Access to 3‐Substituted Quinoxalin‐2‐ones under Superparamagnetic Nanoparticle Catalysis

Nguyen

Phan

et al. 2018

ChemistrySelect

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Fe2O3 superparamagnetic nanoparticles emerged as a productive recyclable heterogeneous catalyst for the cyclization reaction between α‐keto acids and benzene‐1,2‐diamines to produce quinoxalinones as major products and benzimidazoles as minor products. The Fe2O3 nanoparticles displayed higher activity in the synthesis of quinoxalinones than a series of nano catalysts as well as iron‐, copper‐, nickel‐, and cobalt‐based homogeneous catalysts. Moreover, the Fe2O3 nanoparticles was easily recovered by magnetic decantation, and was reutilized without a remarkable deterioration in catalytic activity and selectivity towards quinoxalinones. To our best knowledge, this transformation was not previously conducted under heterogeneous catalysis conditions.

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Expanding the Potential of 3‐Hydroxyindolinones: Synthesis of Quinoxalin‐2(1H)‐ones through Acid‐Promoted Azidation and Ring‐Expansion

Zhan,

Xu,

Guo

et al. 2023

Adv Synth Catal

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We report herein a synthesis of quinoxalin‐2(1H)‐ones from 3‐hydroxyindolin‐2‐one derivatives, which can be synthesized from commercially available isatins in one or two steps. The reaction proceeded through a CF3CO2H‐mediated azidation via a carbocation, followed by acid‐induced N2 extrusion and ring‐expansion. Both CF3CO2H and the solvent 1,1,1,3,3,3‐hexafluoro‐2‐propanol were found to be crucial for this rearrangement. The axial chirality in 3‐hydroxyindolin‐2‐one skeleton was fully preserved in the products.

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An Efficient Synthetic Protocol for Quinoxalinones, Benzoxazinones, and Benzothiazinones from 2‐Oxo‐2‐aryl‐acetyl Bromide Precursors

Cited by 19 publications

References 28 publications

Metal-Free sp3 C-H Bond Oxidation and Functionalization of α-Bromoketones to Quinoxalinone, Benzoxazinone, and Benzothiazinone Heterocyclic Compounds

Metal-Free sp3 C-H Bond Oxidation and Functionalization of α-Bromoketones to Quinoxalinone, Benzoxazinone, and Benzothiazinone Heterocyclic Compounds

Ready Access to 3‐Substituted Quinoxalin‐2‐ones under Superparamagnetic Nanoparticle Catalysis

Expanding the Potential of 3‐Hydroxyindolinones: Synthesis of Quinoxalin‐2(1H)‐ones through Acid‐Promoted Azidation and Ring‐Expansion

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