A Green Approach to the Synthesis of Novel Indole Substituted 2-Amino- 4,5-dihydro-3-furancarbonitriles in Water

2019 ◽  
Vol 16 (3) ◽  
pp. 209-214
Author(s):  
Pannala Padmaja ◽  
Pedavenkatagari Narayana Reddy ◽  
Bijaya Ketan Sahoo
Keyword(s):  
Sodium Borohydride ◽  
Room Temperature ◽  
Efficient Synthesis ◽  
One Pot ◽  
Catalyst Free ◽  
Green Approach ◽  
Three Component Reaction ◽  
Wide Range ◽  
Synthetic Utility ◽  
Synthetic Intermediates

2-Amino-4,5-dihydro-3-furancarbonitriles (ADFCs) have attracted much attention due to their utility as valuable synthetic intermediates for the preparation of a series of acyclic and cyclic organic compounds. On the other hand, indoles substituted with furans are highly interesting compounds displaying a wide range of biological and pharmaceutical activities. However, to the best of our knowledge, indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles have not been previously reported. A new and efficient synthesis of indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles has been developed in two steps using water as a solvent. The first step of the sequence involves threecomponent reaction of phenylglyoxals, indoles and malononitrile under aqueous and catalyst-free conditions for the synthesis of indole substituted β,β-dicyanoketones. Reduction of the obtained β,β- dicyanoketones with sodium borohydride in water at room temperature afforded the indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles in good yields. Several substituted phenylglyooxals were reacted smoothly with indole or 2-methylindole and malononitrile to give the corresponding indole substituted β,β-dicyanoketones in good yields. Treatment of the obtained β,β-dicyanoketones with sodium borohydride in water furnished exclusively the indole substituted 2-amino-4,5-dihydro-3- furancarbonitriles in good yields. We have developed an efficient straightforward access to indole substituted β,β-dicyanoketones by one-pot three-component reaction of phenylglyoxals, indoles and malononitrile. The synthetic utility of obtained indole substituted β,β-dicyanoketones has been outlined by the preparation of indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles. The advantage of catalyst-free, atom-economical and environmental benignity render it promising methods for preparation of indole substituted 2-amino-4,5-dihydro-3-furancarbonitriles.

Aqueous, One-Pot, Three-Component Reaction for Efficient Synthesis of 2-[4-(Arylsulfonyl)piperazin-1-yl]-1,3-benzothiazole, ‑1H-benzimidazole, or -1,3-benzoxazole Derivatives

Synlett ◽  
2017 ◽  
Vol 28 (17) ◽  
pp. 2295-2298
Author(s):  
Kommula Dileep ◽  
M. Murty
Keyword(s):  
Room Temperature ◽  
Efficient Synthesis ◽  
One Pot ◽  
Three Component Reaction ◽  
Aqueous Conditions

A simple and efficient synthetic protocol has been developed involving a one-pot three-component reaction of a 2-chlorobenzazole, piperazine, and an arenesulfonyl chloride under aqueous conditions at room temperature in the absence of a catalyst, ligand, or base. By using this protocol, a variety of 2-[4-(arylsulfonyl)piperazin-1-yl]-1,3-benzothiazole, -1H-benzimidazole, and -1,3-benzoxazole derivatives were synthesized in excellent yields.

scholarly journals A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

2019 ◽  
Vol 15 ◽  
pp. 1523-1533 ◽  
Author(s):  
András György Németh ◽  
György Miklós Keserű ◽  
Péter Ábrányi-Balogh
Keyword(s):  
Elemental Sulfur ◽  
Building Blocks ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
Synthetic Procedure ◽  
Three Component Reaction ◽  
Wide Range ◽  
Organic Chemist ◽  
The One

A new multicomponent reaction has been developed between isocyanides, sulfur and alcohols or thiols under mild reaction conditions to afford O-thiocarbamates and dithiocarbamates in moderate to good yields. The one-pot reaction cascade involves the formation of an isothiocyanate intermediate, thus a catalyst-free synthesis of isothiocyanates, as valuable building blocks from isocyanides and sulfur is proposed, as well. The synthetic procedure suits the demand of a modern organic chemist, as it tolerates a wide range of functional groups, it is atom economic and easily scalable.

CuI/Et2NH-Catalyzed One-Pot Highly Efficient Synthesis of 1,4-Disubstituted 1,2,3-Triazoles in Green Solvent Glycerol

Synthesis ◽  
2018 ◽  
Vol 50 (11) ◽  
pp. 2191-2199 ◽  
Author(s):  
Yongde Zhao ◽  
Shengqiang Guo ◽  
Yang Zhou ◽  
Bencai Dai ◽  
Cuimeng Huo ◽  
...  
Keyword(s):  
Catalytic System ◽  
Sodium Azide ◽  
Room Temperature ◽  
Green Solvent ◽  
Efficient Synthesis ◽  
One Pot ◽  
Highly Efficient ◽  
Three Component Reaction ◽  
Efficient Route ◽  
Terminal Acetylenes

A concise one-pot three-component reaction of organic halides­, terminal acetylenes, and sodium azide provided an efficient route for the synthesis of 1,2,3-triazoles. A variety of 1,2,3-triazoles were prepared in good to excellent yields with green solvent glycerol. This procedure used CuI and diethylamine, which are two easily available reagents as the new catalytic system at room temperature.

Ionic liquid promoted simple and efficient synthesis of β-enamino esters and β-enaminones from 1,3-dicarbonyl compounds – One-pot, three-component reaction for the synthesis of substituted pyridines

2005 ◽  
Vol 83 (10) ◽  
pp. 1746-1751 ◽  
Author(s):  
Ganesan Karthikeyan ◽  
Paramasivan T Perumal
Keyword(s):  
Ionic Liquid ◽  
Room Temperature ◽  
Ammonium Acetate ◽  
Efficient Synthesis ◽  
One Pot ◽  
Dicarbonyl Compounds ◽  
Acidic Ionic Liquid ◽  
Brønsted Acidic Ionic Liquid ◽  
Three Component Reaction ◽  
Substituted Pyridines

A facile enamination of 1,3-dicarbonyl compounds with amines has been developed that affords good to excellent yields of β-enamino esters and β-enaminones using Brønsted acidic ionic liquid 1-methylimidazolium trifluoroacetate ([Hmim]+Tfa–) at room temperature. This methodology has been extended for the synthesis of substituted pyridines in excellent yield by a one-pot, three-component reaction of 1,3-dicarbonyl compounds, ammonium acetate, and alkynone in the presence of [Hmim]+Tfa–.Key words: ionic liquid, β-enaminones, β-enamino esters, 1,3-dicarbonyl compounds, amines, pyridines.

K2S2O8-Mediated Arylmethylation of Indoles with Tertiary Amines via sp3 C–H Oxidation in Water

Synlett ◽  
2018 ◽  
Vol 29 (17) ◽  
pp. 2306-2310 ◽  
Author(s):  
Lal Yadav ◽  
Rana Singh ◽  
Manjula Singh ◽  
Arvind Yadav
Keyword(s):  
Transition Metal ◽  
Room Temperature ◽  
Tertiary Amines ◽  
Efficient Synthesis ◽  
One Pot ◽  
Catalyst Free ◽  
Highly Efficient

A transition-metal- and catalyst-free, highly efficient synthesis of 3-arylmethylindoles has been achieved using tertiary amines as both methylene (-CH2-) transfer and arylmethylation agents and K2S2O8 as a convenient oxidant. The key feature of this protocol is the utilisation of K2S2O8 as an inexpensive and easy to handle radical surrogate that can effectively promote the reaction, leading to the formation of C(sp2)–C(sp3)–C(sp2) bonds via sp3 C–H bond oxidation in water at room temperature in a one-pot procedure.

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

scholarly journals Clean one-pot multicomponent synthesis of pyrans using a green and magnetically recyclable heterogeneous nanocatalyst

SynOpen ◽  
2021 ◽  
Author(s):  
Mina Ghassemi ◽  
Ali Maleki
Keyword(s):  
Room Temperature ◽  
Significant Loss ◽  
Copper Ferrite ◽  
Multicomponent Synthesis ◽  
Thermo Gravimetric ◽  
Sem Images ◽  
One Pot ◽  
Three Component Reaction ◽  
Ft Ir ◽  
The One

Copper ferrite (CuFe2O4) magnetic nanoparticles (MNPs) were synthesized via thermal decomposition method and applied as a reusable and green catalyst in the synthesis of functionalized 4H-pyran derivatives using malononitrile, an aromatic aldehyde and a β-ketoester in ethanol at room temperature. Then it was characterized by Fourier transform infrared spectroscopy (FT-IR), energy-dispersive X-ray spectroscopy (EDX) analysis, scanning electron microscopy (SEM) images, thermo gravimetric and differential thermo gravimetric (TGA/DTG) analysis. The catalyst was recovered from the reaction mixture by applying an external magnet and decanting the mixture. Recycled catalyst was reused for several times without significant loss in its activity. Running the one-pot three-component reaction at room temperature, no use of eternal energy source and using a green solvent provide benign, mild, and environmentally friendly reaction conditions; as well, ease of catalyst recovering, catalyst recyclability, no use of column chromatography and good to excellent yields are extra advantages of this work.

Synthesis of isoxazolidines via catalyst-free one-pot three-component cycloaddition of sulfoxonium ylides, nitrosoarenes and alkenes

2021 ◽  
Author(s):  
Xing Li ◽  
Pingan Zhai ◽  
Yongsheng Fang ◽  
Wenhui Li ◽  
Honghong Chang ◽  
...  
Keyword(s):  
One Pot ◽  
Catalyst Free ◽  
Practical Strategy ◽  
Three Component Reaction

A general and practical strategy for the construction of various keto-substituted isoxazolidines via one-pot three-component reaction of easily accessible, safer and more stable sulfoxonium ylides, nitrosoarenes and olefins is described.

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