NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides

Barak, Dinesh S.; Mukhopadhyay, Sushobhan; Dahatonde, Dipak J.; Batra, Sanjay

doi:10.1016/j.tetlet.2018.12.025

Cited by 8 publications

(11 citation statements)

References 35 publications

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“…To prove the practicality of the reaction, cyclization of compound 2 b was performed, [15] providing the corresponding product 3 b in 80% yield (Scheme 3). Many reports disclosed that 1,2,3‐benzotriazin‐4(3H)‐one is an important heterocyclic skeleton in pharmaceuticals and bioactive molecules.…”

Section: Methodsmentioning

confidence: 99%

“…The reaction temper-ature was screened as well. When the reaction was carried out at 90 °C, 80 °C, and 75 °C for 2 h, the corresponding product was formed in 11%, 70%, and 62% yield, respectively (entries [13][14][15]. Importantly, the choice of the reaction time was found to be crucial, where decreasing the reaction time to 1 h can promote the targeted transformation (73% yield) (entries 16-18).…”

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confidence: 99%

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Catalyst‐Free Hydrogen Proton Transfer Reduction of Nitrobenzamides to Aminobenzamides with iPrOH/KOH System

et al. 2021

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A reduction of nitrobenzenes via the combination of KOH and isopropanol was established for the general synthesis of aniline derivatives. A metal catalyst isn't required in this alternative reduction reaction, and a series of nitrobenzamide compounds were chemoselectively reduced into the corresponding aminobenzamides in good to excellent yields. This reaction is operationally simple, and proceeds under mild conditions.

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Section: Methodsmentioning

confidence: 99%

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confidence: 99%

Catalyst‐Free Hydrogen Proton Transfer Reduction of Nitrobenzamides to Aminobenzamides with iPrOH/KOH System

et al. 2021

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“…In addition, AcOH could promote this reaction better than oxalic acids and fumaric acid (entry 11, [13][14][15]. The bases showed negative effect on this transform due to possibly inhibit the formation of 2-nitrosobenzoic acid (entry [16][17][18].…”

Section: Scheme 1 Synthesis Of 2-aminobenzamidesmentioning

confidence: 99%

“…Acetone was the best solvent in our case and the yield of 4a increased to 69% by controlling the amount of acetone (entries 2, 4-12). In addition, AcOH promoted this reaction better than oxalic acid and fumaric acid (entries 11,[13][14][15]. The addition of a base showed a negative effect on this transform due to the possibly inhibition of the formation of 2-nitrosobenzoic acid (entries [16][17][18].…”

Section: Feature Synthesismentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8][9][10][11] These skeletons could be easily synthesized from 2-aminobenzamides. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Besides, these 2-aminobenzamides scaffolds also exist in various biological active agents such as anticancer, antimicrobial, anti-inflammatory, anticonvulsant, anti-tubercular, antiviral, and antimalarial agents. 1,6,9,11 Therefore, the synthesis of 2-aminobenzamides plays an important role in organic synthesis.…”

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confidence: 99%

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UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes To Give 2-Aminobenzamides

et al. 2022

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A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

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Recent Advances in Denitrogenative Organic Transformations of 1,2,3‐Benzotriazin‐4(3H)‐ones

Madasamy

2024

Asian J Org Chem

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Denitrogenative organic transformations and related reactions are a class of significant approaches for carrying out unusual C−C/C‐heteroatom (C−O, C−N, C−S) bond‐forming reactions that are usually promoted by Ru, Ir, Pd, Ni, and Cu metal catalysts. In this trait, numerous methods were adopted to synthesize several pharmaceutically valuable N‐ and O‐containing heteroaromatics using 1,2,3‐benzotriazin‐4(3H)‐one as an electrophilic coupling partner. This review involves the recent achievements related to the metal/organo‐catalyzed thermal and visible‐light mediated denitrogenative approaches with 1,2,3‐benzotriazin‐4(3H)‐ones towards the synthesis of imperative N‐heteroaromatic compounds. In addition, metal and oxidant‐free ortho‐functionalization of benzotriazinones by using suitable nucleophilic partners have been discussed. In particular, the most novel methods employing Ni and Pd metal catalysts that have emerged are exhibited. Specific attention has been paid to offering the detailed mechanistic pathway to explain the role of metal catalysts and the mechanism in the absence of metal catalysts in the denitrogenative reactions under a thermal/visible light medium.

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NaNO2/I2 as an alternative reagent for the synthesis of 1,2,3-benzotriazin-4(3H)-ones from 2-aminobenzamides

Cited by 8 publications

References 35 publications

Catalyst‐Free Hydrogen Proton Transfer Reduction of Nitrobenzamides to Aminobenzamides with iPrOH/KOH System

Catalyst‐Free Hydrogen Proton Transfer Reduction of Nitrobenzamides to Aminobenzamides with iPrOH/KOH System

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes To Give 2-Aminobenzamides

Recent Advances in Denitrogenative Organic Transformations of 1,2,3‐Benzotriazin‐4(3H)‐ones

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