“On water” cascade synthesis of benzopyranopyrazoles and their macrocycles

Muthusamy, Sengodagounder; Gangadurai, Chinnakuzhanthai

doi:10.1016/j.tetlet.2018.03.013

Cited by 14 publications

(6 citation statements)

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“…The 2-hydroxyarylaldehydes were O -alkylated with alkyl 2-bromoacetate, benzyl chloride, allyl bromide, propargyl bromide, and 2-bromoacetonitrile following the reported procedure. 22 , 23 , 25 Unless otherwise mentioned, all sulfinates were synthesized following the experimental procedure mentioned below.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…N -Arylsulfonylhydrazides used for the synthesis N -arylsulfonylhydrazones were obtained following the reported , procedure from commercially available sulfonyl chlorides and hydrazine hydrate. The 2-hydroxyarylaldehydes were O -alkylated with alkyl 2-bromoacetate, benzyl chloride, allyl bromide, propargyl bromide, and 2-bromoacetonitrile following the reported procedure. ,, Unless otherwise mentioned, all sulfinates were synthesized following the experimental procedure mentioned below.…”

Section: Experimental Sectionmentioning

confidence: 99%

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K₂CO₃-Catalyzed Rapid Conversion of N-Sulfonylhydrazones to Sulfinates

Korawat

Basak

2020

ACS Omega

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N -Sulfonylhydrazones derived from alkyl, aryl, and heteroaryl aldehydes and ketones undergo rapid conversion into the corresponding sulfinates when heated with 10 mol % K 2 CO 3 in N , N ′-dimethylethylene urea (DMEU) at elevated temperature. The reaction conditions are amenable to several functional groups and suitable for gram-scale synthesis. Under these base-catalyzed conditions, N -tosylhydrazones derived from O -allylated and O -propargylated 2-hydroxyarylaldehydes do not undergo the well-established intramolecular [3 + 2]-cycloaddition reactions and generate corresponding sulfinates in good yields. The base-catalyzed transformation proceeds via crucial rapid intermolecular protonation of the diazo intermediate 11 to generate diazonium ion 12 , which upon nucleophilic displacement by the sulfonyl ion 10 provides the desired sulfinate selectively.

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Section: Experimental Sectionmentioning

confidence: 99%

Section: Experimental Sectionmentioning

confidence: 99%

K₂CO₃-Catalyzed Rapid Conversion of N-Sulfonylhydrazones to Sulfinates

Korawat

Basak

2020

ACS Omega

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“…Another on water chemistry for the synthesis of benzopyrazoles was explored by S. Muthusamy et al . The reaction of different salicylaldehydes with propargyl bromide in DMF using K 2 CO 3 as a base at 0 °C to room temperature furnished the desired propargylatedsalicylaldehydes.…”

Section: Cycloaddition Reactions On Watermentioning

confidence: 99%

Recent Advances and Prospects of Organic Reactions “On Water”

et al. 2019

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Organic reactions “On water” is a rapidly developing area over the past few years. Many important classes of reactions like cross‐coupling reactions, pericyclic reactions, C−H activations etc. were performed on water and have shown tremendous increase in the reaction rates due to the potential hydrogen bonding capacity of water. This review focuses on the recent trends and developments in the field of on water reactions applied to organic synthesis and covers literature from 2016–2019.

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“…Performing organic reactions into the green solvents especially water is very favorable for academic researchers and industrial chemical companies due to its many desirable features such as low-cost, non-toxicity, safety, abundantly and also environmentally friendless compared with organic solvents [1][2][3][4][5][6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Two different facile and efficient approaches for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 nanoparticles in water

Zeynizadeh

Aminzadeh

Mousavi

2019

Green Processing and Synthesis

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Two simple, efficient, and environmentally benign protocols for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of aromatic nitro compounds promoted by CuFe2O4 nanoparticles in water at reflux have been developed. The prepared CuFe2O4 MNPs are well known and fully characterized by various techniques. Furthermore, the CuFe2O4 NPs easily separated from the reaction environment using an external magnetic field and can be reused for several times without significant loss of its activity for both mentioned reactions.

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“On water” cascade synthesis of benzopyranopyrazoles and their macrocycles

Cited by 14 publications

References 50 publications

K₂CO₃-Catalyzed Rapid Conversion of N-Sulfonylhydrazones to Sulfinates

K₂CO₃-Catalyzed Rapid Conversion of N-Sulfonylhydrazones to Sulfinates

Recent Advances and Prospects of Organic Reactions “On Water”

Two different facile and efficient approaches for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 nanoparticles in water

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“On water” cascade synthesis of benzopyranopyrazoles and their macrocycles

Cited by 14 publications

References 50 publications

K2CO3-Catalyzed Rapid Conversion of N-Sulfonylhydrazones to Sulfinates

K2CO3-Catalyzed Rapid Conversion of N-Sulfonylhydrazones to Sulfinates

Recent Advances and Prospects of Organic Reactions “On Water”

Two different facile and efficient approaches for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 nanoparticles in water

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About

K₂CO₃-Catalyzed Rapid Conversion of N-Sulfonylhydrazones to Sulfinates

K₂CO₃-Catalyzed Rapid Conversion of N-Sulfonylhydrazones to Sulfinates