A basic ionic liquid catalyzed reaction of benzothiazole, aldehydes, and 5,5‐dimethyl‐1,3‐cyclohexanedione: Efficient synthesis of tetrahydrobenzo[<i>b</i>]pyrans

Wen, Li‐Rong; Xie, Huai-Yuan; Li, Ming

doi:10.1002/jhet.183

Cited by 17 publications

(4 citation statements)

References 36 publications

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“…A facile, mild, and quantitative procedure for the preparation of tetrahydrobenzo [b] pyran derivatives in the presence of an easily accessible basic ionic liquid [bmim]OH as catalyst has been developed by Wen et al [114]. The ionic liquid was used for at least nine times with consistent activity (see Scheme 11).…”

Section: As Base Catalysts Basic Functionalized Ionic Liquids Havementioning

confidence: 99%

Ionic Liquids: Synthesis and Applications in Catalysis

Rajni

2014

Advances in Chemistry

217

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Ionic liquids have emerged as an environmentally friendly alternative to the volatile organic solvents. Being designer solvents, they can be modulated to suit the reaction conditions, therefore earning the name "task specific ionic liquids. " Though primarily used as solvents, they are now finding applications in various fields like catalysis, electrochemistry, spectroscopy, and material science to mention a few. The present review is aimed at exploring the applications of ionic liquids in catalysis as acid, base, and organocatalysts and as soluble supports for catalysts.

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Section: As Base Catalysts Basic Functionalized Ionic Liquids Havementioning

confidence: 99%

Ionic Liquids: Synthesis and Applications in Catalysis

Rajni

2014

Advances in Chemistry

217

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“…In the interest of the aforementioned suggestion, Knoevenagel condensation of 5‐bromosalicylaldehyde ( 1 ) with 2‐(4‐(2‐oxo‐2 H ‐chromen‐3‐yl)thiazol‐2‐yl)acetonitrile ( 2a ) , 2‐(4‐(5‐bromobenzofuran‐2‐yl)thiazol‐2‐yl)acetonitrile ( 2b ) , 3‐(5‐bromobenzofuran‐2‐yl)‐3‐oxopropanenitrile ( 2c ), and 2‐(benzo[ d ]thiazol‐2‐yl)acetonitrile ( 2d ) under solvent‐free condition led to formation of the corresponding iminocoumarins 3a–d , respectively (Scheme ). The structure of the reaction products was ascertained on the basis of their elemental analysis and spectral data, where the IR spectra showed the absence of cyano function and displayed an absorption bands at 3280–3210 cm −1 characteristic to NH group.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Evaluation of Antimicrobial Activity of Some Novel Heterocyclic Compounds from 5‐Bromosalicylaldehyde

Abdel‐Aziem

Baaiu

Abdelhamid

2017

Journal of Heterocyclic Chem

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A novel series of coumarins, thiadiazoles, thiazoles, and pyridines were synthesized via reaction of 5‐bromosalicylaldehyde with different reagents. Thus, 5‐bromosalicylaldehyde 1 was reacted with compounds 2a–d affording iminocoumarins 3a–d, which on hydrolysis with 10% hydrochloric acid, afforded coumarins 4a–d, respectively. On the other hand, reaction of 1 with benzylhydrazinecarbodithioate 5 afforded derivative 6, which reacted with hydrazonoyl halides 7a–f, afforded 1,3,4‐thiadiazoles 11a–f, respectively. Moreover, thiazoles 15 and 16 were obtained via reaction of 1 with thiocarbohydrazide 13 and hydrazonoyl halides. However, condensation of 2‐acetyl‐5‐bromobenzofuran 17 with benzaldehyde afforded chalcone 18, which reacted with pyridiniumbromides 19a–c, afforded pyridines 20a–c, respectively. Furthermore, pyridines 21–24 were synthesized from the reaction of chalcone 18 with different active methylene compounds. Reaction of 24 with ethylchloroacetate, chloroacetone, and chloroacetonitrile afforded thienopyridines 26a–c, respectively. The structures of the newly synthesized compounds were established based on their spectral data and elemental analyses. Also, selected newly synthesized compounds were screened for their antimicrobial activity against various microorganisms by disk diffusion method.

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“…nanoparticles, [25] DBU, [26] Fe(HSO 4 ) 3 , [27] Ce(SO 4 ) 2 .4H 2 O, [28] and ionic liquid [29] have made tremendous progress in the past years, this reaction still has limitations including nongeneralization, use of excess amount of expensive catalysts, harsh reaction condition, low yields, and long reaction time. Therefore, an ideal protocol would install the desired pyran scaffolds in a time-efficient and one-pot procedure.…”

Section: Introductionmentioning

confidence: 99%