scholarly journals Synthesis of α-amino amidines through molecular iodine-catalyzed three-component coupling of isocyanides, aldehydes and amines

2014 ◽  
Vol 10 ◽  
pp. 2065-2070 ◽  
Author(s):  
Praveen Reddy Adiyala ◽  
D Chandrasekhar ◽  
Jeevak Sopanrao Kapure ◽  
Chada Narsimha Reddy ◽  
Ram Awatar Maurya
Keyword(s):  
Environmental Impact ◽  
Coupling Reaction ◽  
Molecular Iodine ◽  
Atom Economy ◽  
Reaction Conditions ◽  
High Yields ◽  
Three Component Coupling

A facile and efficient synthetic protocol for the synthesis of α-amino amidines has been developed using a molecular iodine-catalyzed three-component coupling reaction of isocyanides, amines, and aldehydes. The presented strategy offers the advantages of mild reaction conditions, low environmental impact, clean and simple methodology, high atom economy, wide substrate scope and high yields.

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 PEG-embedded KBr3: A recyclable catalyst for multicomponent coupling reaction for the efficient synthesis of functionalized piperidines

2011 ◽  
Vol 7 ◽  
pp. 1334-1341 ◽  
Author(s):  
Sanny Verma ◽  
Suman L Jain ◽  
Bir Sain
Keyword(s):  
Coupling Reaction ◽  
Recyclable Catalyst ◽  
Efficient Synthesis ◽  
Molecular Bromine ◽  
Keto Ester ◽  
One Step ◽  
High Yields ◽  
Multicomponent Coupling ◽  
Three Component Coupling

PEG-embedded potassium tribromide ([K+PEG]Br3 −) was found to be an efficient and recyclable catalyst for the synthesis of functionalized piperidines in high yields in a one step, three component coupling between aldehyde, amine and β-keto ester. At the end of the reaction the [K+PEG]Br3 − was readily regenerated from the reaction mixture by treating the residue containing [K+PEG]Br− with molecular bromine.

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

I2-Catalyzed Oxidative Coupling of Ketone Oximes and Dialkyl/Diarylphosphine Oxides

Synlett ◽  
2020 ◽  
Vol 32 (01) ◽  
pp. 75-80
Author(s):  
Qingle Zeng ◽  
Nutao Li ◽  
Yiding Wang ◽  
Hongqin Yang ◽  
Ze He
Keyword(s):  
Hydrogen Peroxide ◽  
Oxidative Coupling ◽  
Molecular Iodine ◽  
Oxidizing Agent ◽  
Atom Economy ◽  
High Yields

AbstractA new protocol for the oxidative coupling of ketone oximes with dialkyl/diarylphosphine oxides to synthesize O-(dialkylphosphinyl)ketone oximes has been developed. Hydrogen peroxide is used as a green oxidizing agent, and molecular iodine is used as a nonmetal catalyst. The reaction has a high atom economy, with water as the only byproduct. O-(Dialkylphosphinyl)ketone oximes with 26 examples have been obtained with high yields. Furthermore, the product may be transformed into other molecules, i.e., by reduction.

scholarly journals Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

2019 ◽  
Vol 15 ◽  
pp. 874-880
Author(s):  
Razieh Navari ◽  
Saeed Balalaie ◽  
Saber Mehrparvar ◽  
Fatemeh Darvish ◽  
Frank Rominger ◽  
...  
Keyword(s):  
Room Temperature ◽  
High Selectivity ◽  
Domino Reaction ◽  
Primary Amines ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Efficient Approach ◽  
Three Component Reaction ◽  
High Yields

An efficient approach for the synthesis of pyrazolopyridines containing the aminochromane motif through a base-catalyzed cyclization reaction is reported. The synthesis was carried out through a three-component reaction of (arylhydrazono)methyl-4H-chromen-4-one, malononitrile, primary amines in the presence of Et3N at room temperature. However, carrying out the reaction under the same conditions without base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach.

A bromine-radical mediated three-component reaction comprising allenes, electron-deficient alkenes and allyl bromides: facile synthesis of 2-bromo-1,7-dienes

2014 ◽  
Vol 50 (45) ◽  
pp. 5993-5996 ◽  
Author(s):  
Takashi Kippo ◽  
Ilhyong Ryu
Keyword(s):  
Coupling Reaction ◽  
Facile Synthesis ◽  
Three Component Reaction ◽  
High Yields ◽  
Three Component Coupling

A bromine-radical mediated three-component coupling reaction was effectively achieved by the use of allenes, electron-deficient alkenes, and allyl bromides and led to the synthesis of 2-bromo-1,7-dienes in good to high yields.

Dimerization of Aromatic Compounds Using Palladium-Carbon-Catalyzed Suzuki–Miyaura Cross-Coupling by One-Pot Synthesis

Synlett ◽  
2018 ◽  
Vol 29 (06) ◽  
pp. 779-784 ◽  
Author(s):  
Guoliang Chen ◽  
Fangyu Du ◽  
Qifan Zhou ◽  
Dongdong Liu ◽  
Ting Fang ◽  
...  
Keyword(s):  
Aromatic Compounds ◽  
Functional Group ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Potassium Acetate ◽  
Carbon Catalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
High Yields

The aromatic dimers play a significant role in many aspects. Herein, we report a simple palladium-carbon catalyst that is highly effective for the dimerization of brominated aromatic compounds under mild conditions using abundant brominated aromatic compounds, bis(pinacolate)diboron and potassium acetate by a ‘one-pot’ method. This process, which we believe proceeds via a Suzuki–Miyaura cross-coupling reaction mechanism, allows access to a variety of aromatic compounds under mild reaction conditions and has a good functional group tolerance with moderate to high yields.

Synthesis of New 5-amino-7-(aryl)-1,2,3,7-tetrahydro-8-nitroimidazo[1,2-a]pyridine- 6-carboxamide and 6-amino-2,3,4,8-tetrahydro-9-nitro-8-(aryl)-1H-pyrido[1,2- a]pyrimidine-7-carboxamide Derivatives

2018 ◽  
Vol 15 (7) ◽  
pp. 982-988 ◽  
Author(s):  
Fahimeh S. Hosseini ◽  
Mohammad Bayat
Keyword(s):  
Aromatic Aldehydes ◽  
Chromatographic Technique ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Synthetic Routes ◽  
High Yields ◽  
Work Up ◽  
Optimal Reaction

Aim and Objectives: Development of simple synthetic routes for widely used organic compounds from readily available reagents is one of the major tasks in organic chemistry. Therefore, new approaches for increasing the molecular diversity of simple starting materials, are needed. Herein, an efficient synthesis of imidazo[1,2-a]pyridine, pyrido[1,2-a]pyrimidine and pyrido[1,2-a][1,3]diazepine derivatives is described. Materials and Methods: A one-pot, multi-component reaction of nitro ketene aminal derived from the addition of various 1,n-diamines to 1,1-bis(methylthio)-2-nitroethene with cyanoacetamide and aromatic aldehydes is described. The reactions are completed within 2-5 h, in ethanol at reflux, in good to high yields (70-93%). The structures of products were deduced from their IR, mass, 1H NMR, and 13C NMR spectra. Results: Optimal reaction conditions for the synthesis of products were obtained, when ethanol was used as the solvent at reflux. This protocol involves Michael reaction, imine–enamine tautomerization, and cyclization sequences. Conclusion: This work represents an efficient synthesis of imidazo[1,2-a]pyridine, pyrido[1,2-a]pyrimidine and pyrido[1,2-a][1,3]diazepine derivatives via a one-pot, multi-component reaction. The advantages of this protocol are mild conditions, easy accessibility of reactants, absence of catalyst, high atom economy, simple work-up and purification process with no chromatographic technique.

A Simple and Economic Synthesis of Propargylamines by CuI-Catalyzed Three-Component Coupling Reaction with Succinic Acid as Additive

2009 ◽  
Vol 62 (1) ◽  
pp. 75 ◽  
Author(s):  
Gerui Ren ◽  
Jinli Zhang ◽  
Zheng Duan ◽  
Mengjun Cui ◽  
Yangjie Wu
Keyword(s):  
Succinic Acid ◽  
Efficient Method ◽  
Coupling Reaction ◽  
One Pot ◽  
Wide Range ◽  
High Yields ◽  
Three Component Coupling

A practical and efficient method was developed for the synthesis of propargylamines in a one-pot procedure from aldehydes, amines, and alkynes by using CuI as catalyst and succinic acid as additive. By using this protocol, a wide range of propargylamines was obtained in high yields.

Ionic Liquid Promoted Knoevenagel and Michael Reactions

2004 ◽  
Vol 57 (11) ◽  
pp. 1067 ◽  
Author(s):  
Xuesen Fan ◽  
Xueyuan Hu ◽  
Xinying Zhang ◽  
Jianji Wang
Keyword(s):  
Ionic Liquid ◽  
Knoevenagel Condensation ◽  
Reaction Medium ◽  
Environmentally Benign ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Michael Reactions ◽  
Operation Process ◽  
Benign Nature ◽  
High Yields

The utilization of the ionic liquid [bmim][BF4] as both reaction medium and promoter for the Knoevenagel condensation and Michael addition reactions is described in this paper. Through these reactions, several useful electrophilic alkenes and chromene derivatives are obtained in high yields. The advantages of these two novel procedures include their environmentally benign nature, atom economy, simple operation process, and mild reaction conditions.

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