An efficient method for synthesis of bis(indolyl)methane and di-bis(indolyl)methane derivatives in environmentally benign conditions using TBAHS

Siadatifard, Sayed Hossein; Abdoli‐Senejani, Masumeh; Bodaghifard, Mohammad Ali

doi:10.1080/23312009.2016.1188435

Cited by 27 publications

(8 citation statements)

References 36 publications

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“…As a part of ongoing research into the efficient synthesis of heterocyclic compounds [32][33][34][35][36], in the present study, we describe a green and effective procedure for the Nalkylation of aromatic amines with alcohols using H At first, the reaction of aniline (1 mmol) and benzhydrol (1 mmol) in the presence of 0.05 g of the catalyst in various solvents at 60 o C was selected as a model reaction ( Table 1). The results indicated that, among all, C 2 H 5 OH/H 2 O (1:1) is the most effective solvent.…”

Section: Resultsmentioning

confidence: 99%

Phosphomolybdic acid immobilized chitosan/Fe3O4: an efficient catalyst for the N-alkylation of anilines

Ghanimati¹,

Abdoli‐Senejani²,

Bodaghifard³

et al. 2020

Eurasian Chem. Commun.

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In this work, phosphomolybdic acid immobilized on chitosan/Fe3O4 as a green catalyst was used for the Hofmann Nalkylation of aniline derivatives with alcohols. H3PMo12O40/chitosan/Fe3O4 (PMo/Chit/Fe3O4) was prepared from the phosphomolybdic acid, chitosan, and Fe3O4 MNPs. Several secondary amines were synthesized from primary arylamines with electron-donating, electron-withdrawing groups, and alcohols in good to excellent yields. The catalyst could be separated using an external magnet and recovered without reducing its catalytic activity. The optimization of the reaction conditions was evaluated using the response surface method (RSM), involving the Box-Behnken design matrix. The simple procedure, only one byproduct (i.e., water), good to excellent yields, easy separation of the catalyst, short reaction times, and environmentally benign conditions were some advantages of this method.

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Section: Resultsmentioning

confidence: 99%

Phosphomolybdic acid immobilized chitosan/Fe3O4: an efficient catalyst for the N-alkylation of anilines

Ghanimati¹,

Abdoli‐Senejani²,

Bodaghifard³

et al. 2020

Eurasian Chem. Commun.

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“…In continuation of our studies of mild and green synthesis of heterocyclic compounds, [16][17][18][19][20] herein we report a new, efficient and environmentally friendly method for the synthesis of N-alkylated amines using Fe(ClO 4 ) 3 /SiO 2 as catalyst (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO₂ as a catalyst through Box–Behnken experimental design

Ghanimati

Abdoli‐Senejani

Isfahani

et al. 2018

Applied Organom Chemis

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Funding information Islamic Azad University-Arak BranchAn efficient method for the N-alkylation of poorly nucleophilic amines using ferric perchlorate immobilized on SiO 2 as a catalyst is described. Fe(ClO 4 ) 3 was prepared from mixing iron(III) hydroxide and perchloric acid and adsorbed on silica gel. The catalyst was characterized using various techniques. The supported ferric perchlorate (Fe(ClO 4 ) 3 /SiO 2 ) revealed high efficiency and selectivity for N-alkylation of aromatic amines with alcohols to provide alkylated amines. Various secondary amines were synthesized from primary amines and alcohols in good to excellent yields, with water as the only by-product. The optimization of the reaction conditions was investigated using the response surface method, and involving the Box-Behnken design matrix. The conditions for optimal reaction yield and time were: amount of catalyst = 0.34 mmol, temperature = 60°C and molar ratio of amine to alcohol = 1.2.The catalyst was recovered and reused for five cycles without a considerable decrease in catalytic activity. The stability of the recycled catalyst was investigated. The proposed method has numerous advantages including procedure simplicity, short reaction times, low cost, good to excellent yields, reusability of the catalyst and mild and environmentally benign conditions.

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“…Several products containing bis(indolyl)alkane derivatives have been separated previously from marine sources 28, 29 . In this regard, various methods have been reported for the synthesis of bis(indolyl)alkane derivatives, especially bis(indolyl)methanes, through electrophilic substitution of indole with carbonyl compounds in the presence of various acid or base catalytic reagents such as ZrO 2 –MgO, 30 tetrabutylammonium hydrogen sulfate, 31 montmorillonite K‐10, 32 zeolite, 33 ammonium chloride, 34 tungstophosphoric acid supported on zirconia, 35 Fe 3 O 4 @silica sulfuric acid, 36 H 5 PW 10 V 2 O 40 /pyridino‐Fe 3 O 4 , 37 nano‐Fe 3 O 4 , 38 ZrO 2 –Al 2 O 3 –Fe 3 O 4 , 39 and [{Ti(salophen)H 2 O} 2 O][OSO 2 C 8 F 17 ] 2 40 . Although these procedures are valuable, some of them have disadvantages.…”

Section: Introductionmentioning

confidence: 99%

3‐Amino‐5‐mercapto‐1,2,4‐triazole‐functionalized Fe₃O₄ magnetic nanocomposite as a green and efficient catalyst for synthesis of bis(indolyl)methane derivatives

Hajibabaei

Abdoli‐Senejani

Shafiei

2020

Applied Organom Chemis

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A core–shell Fe3O4@silica magnetic nanocomposite functionalized with 3‐amino‐5‐mercapto‐1,2,4‐triazole (Fe3O4/SiO2/PTS/AMTA) was prepared using Fe3O4 with silica layer, and its surface was modified with 3‐amino‐5‐mercapto‐1,2,4‐triazole. The novel synthesized magnetite nanocomposite was characterized using various techniques. The catalytic activity of Fe3O4/SiO2/PTS/AMTA was demonstrated in the synthesis of bis(indolyl)methane derivatives under solvent‐free conditions. Some of the bis(indolyl)methane derivatives were synthesized through one‐pot, three‐component reaction of 1 mol of various benzaldehydes or ketones with 2 mol of indole in the presence of Fe3O4/SiO2/PTS/AMTA in good to excellent isolated yields. In addition, the catalyst could be recovered and used for several reaction runs without loss of catalytic activity. The stability of recycled catalyst was investigated. This method has some advantages including experimental simplicity, good to excellent yields, solvent‐free conditions and stability and reusability of the catalyst.

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An efficient method for synthesis of bis(indolyl)methane and di-bis(indolyl)methane derivatives in environmentally benign conditions using TBAHS

Cited by 27 publications

References 36 publications

Phosphomolybdic acid immobilized chitosan/Fe3O4: an efficient catalyst for the N-alkylation of anilines

Phosphomolybdic acid immobilized chitosan/Fe3O4: an efficient catalyst for the N-alkylation of anilines

Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO₂ as a catalyst through Box–Behnken experimental design

3‐Amino‐5‐mercapto‐1,2,4‐triazole‐functionalized Fe₃O₄ magnetic nanocomposite as a green and efficient catalyst for synthesis of bis(indolyl)methane derivatives

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An efficient method for synthesis of bis(indolyl)methane and di-bis(indolyl)methane derivatives in environmentally benign conditions using TBAHS

Cited by 27 publications

References 36 publications

Phosphomolybdic acid immobilized chitosan/Fe3O4: an efficient catalyst for the N-alkylation of anilines

Phosphomolybdic acid immobilized chitosan/Fe3O4: an efficient catalyst for the N-alkylation of anilines

Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO2 as a catalyst through Box–Behnken experimental design

3‐Amino‐5‐mercapto‐1,2,4‐triazole‐functionalized Fe3O4 magnetic nanocomposite as a green and efficient catalyst for synthesis of bis(indolyl)methane derivatives

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Hofmann N‐alkylation of aniline derivatives with alcohols using ferric perchlorate immobilized on SiO₂ as a catalyst through Box–Behnken experimental design

3‐Amino‐5‐mercapto‐1,2,4‐triazole‐functionalized Fe₃O₄ magnetic nanocomposite as a green and efficient catalyst for synthesis of bis(indolyl)methane derivatives