Facile and efficient synthesis of indazole derivatives by 1,3-cycloaddition of arynes with diazo compounds and azomethine imides

2009 ◽  
Vol 74 (6) ◽  
pp. 957-972 ◽  
Author(s):  
Tienan Jin ◽  
Fan Yang ◽  
Yoshinori Yamamoto
Keyword(s):  
Cycloaddition Reaction ◽  
Diazo Compounds ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
High Yields

N-Unsubstituted indazoles 3 and 1-arylindazoles 4 are readily available in good to high yields through [3+2] cycloaddition of 2-(trimethylsilyl)aryl triflates 1 and diazo compounds in the presence of KF or CsF under mild reaction conditions. Furthermore, we found that azomethine imides also underwent cycloaddition reaction with 2-(trimethylsilyl)phenyl triflates (1a) in the presence of KF to afford indazolone derivatives 6 in moderate yields.

scholarly journals A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 3031 ◽  
Author(s):  
Xiaodong Tang ◽  
Songlei Zhu ◽  
Ying Ma ◽  
Ren Wen ◽  
Lanqi Cen ◽  
...  
Keyword(s):  
Environmentally Benign ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Dicarbonyl Compounds ◽  
Pyrrole Derivatives ◽  
Three Component Reaction ◽  
High Yields ◽  
Operational Simplicity

A green, convenient and tandem procedure for the efficient synthesis of highly substituted indeno[1,2-b]pyrrole and acenaphtho[1,2-b]pyrrole derivatives by domino three-component reaction of tryptamine/benzylamine, 1,3-dicarbonyl compounds and ninhydrin/ acenaphthenequinone is described. The significant features of this procedure were characterized by mild reaction conditions, high yields, operational simplicity and it being environmentally benign.

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.

scholarly journals A Solvent-Free Protocol for the Green Synthesis of 5-Arylidene-2,4-thiazolidinediones Using Ethylenediamine Diacetate as Catalyst

2012 ◽  
Vol 2012 ◽  
pp. 1-5 ◽  
Author(s):  
Yuliang Zhang ◽  
Zhongqiang Zhou
Keyword(s):  
Knoevenagel Condensation ◽  
Aromatic Aldehydes ◽  
Solvent Free ◽  
Reusable Catalyst ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Solvent Free Conditions ◽  
High Yields ◽  
Work Up ◽  
Solvent Free Reaction

A simple and efficient synthesis of 5-arylidene-2,4-thiazolidinediones by the Knoevenagel condensation of aromatic aldehydes with 2,4-thiazolidinedione catalyzed by ethylenediamine diacetate under solvent-free conditions is described. The major advantages of this method are simple experimental and work-up procedures, solvent-free reaction conditions, small amount of catalyst, short reaction time, high yields, and utilization of an inexpensive and reusable catalyst.

scholarly journals One-Step Synthesis of Acylboron Compounds via Cu-Catalyzed Carbonylative Borylation of Alkyl Halides

2020 ◽  
Author(s):  
Cheng Li-Jie ◽  
Zhao Siling ◽  
Neal Mankad
Keyword(s):  
Alkyl Halides ◽  
Efficient Synthesis ◽  
Mechanistic Studies ◽  
Acyl Halide ◽  
Reaction Conditions ◽  
One Pot ◽  
One Step ◽  
High Yields ◽  
Tertiary Alkyl

A Cu-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in-situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.<br>

scholarly journals Infrared Irradiation-Assisted Multicomponent Synthesis of 2-Amino-3-cyano-4H-pyran Derivatives

2017 ◽  
Vol 56 (2) ◽  
Author(s):  
Arturo Sánchez ◽  
Fernando Hernández ◽  
Paulo César Cruz ◽  
Yolanda Alcaraz ◽  
Joaquín Tamariz ◽  
...  
Keyword(s):  
Ethyl Acetoacetate ◽  
Present Method ◽  
Reaction Times ◽  
Ammonium Hydroxide ◽  
Infrared Irradiation ◽  
Efficient Synthesis ◽  
Multicomponent Synthesis ◽  
Reaction Conditions ◽  
High Yields ◽  
Pyran Derivative

A simple, versatile, and efficient synthesis of 4<em>H</em>-pyran derivative compounds is achieved via a three-component cyclocondensation of aldehydes, malononitrile, and ethyl acetoacetate, using ammonium hydroxide as the catalyst, promoted by infrared irradiation. The present method offers several advantages, such as high yields, non hazardous reaction conditions as well as short reaction times.

Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a]isoquinolines Bearing Indeno[1,2-b]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 267-271 ◽  
Author(s):  
Firouz Matloubi Moghaddam ◽  
Atiyeh Moafi ◽  
Behzad Jafari ◽  
Alexander Vilinger ◽  
Peter Langer
Keyword(s):  
Cycloaddition Reaction ◽  
Reaction Times ◽  
Dipolar Cycloaddition ◽  
Diastereoselective Synthesis ◽  
X Ray Diffraction ◽  
Reaction Conditions ◽  
One Pot ◽  
Three Component Reaction ◽  
Relative Stereochemistry ◽  
High Yields

A regio- and diastereoselective synthesis of 2,3-dihydro-10b′H-spiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo[2,1-a]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N-ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.

A clean, simple and efficient synthesis of trans-[3-(aryl)-2,3-dihydrofuro[3,2-h] quinolin-2-yl]-(4-chlorophenyl)methanones

2017 ◽  
Vol 41 (7) ◽  
pp. 380-383
Author(s):  
Maryam Salari ◽  
Alireza Hassanabadi ◽  
Mohammad H. Mosslemin
Keyword(s):  
Reaction Time ◽  
Green Chemistry ◽  
Aromatic Aldehyde ◽  
Efficient Method ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
High Yields

We report a green and efficient method for the synthesis of trans-[3-(aryl)-2,3-dihydrofuro[3,2- h]quinolin-2-yl]-(4-chlorophenyl) methanones from the condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with 8-hydroxyquinoline and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in water at reflux conditions. This new protocol employing choline hydroxide, which is a green and inexpensive catalyst, offers advantages such as mild reaction conditions, short reaction time, high yields and does not involve any hazardous solvent. Therefore, this procedure can be classified as green chemistry.

scholarly journals Gold(I)-catalyzed intramolecular cyclization/intermolecular cycloaddition cascade as a fast track to polycarbocycles and mechanistic insights

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Cheng Zhang ◽  
Kemiao Hong ◽  
Chao Pei ◽  
Su Zhou ◽  
Wenhao Hu ◽  
...  
Keyword(s):  
Fast Track ◽  
Cycloaddition Reaction ◽  
Structural Diversity ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
In Situ Formation ◽  
Increasing Demand ◽  
High Yields ◽  
Synthetic Intermediate

AbstractMetal carbene is an active synthetic intermediate, which has shown versatile applications in synthetic chemistry. Although a variety of catalytic methods have been disclosed for the generation of carbene species from different precursors, there is an increasing demand for the development of efficient and practical approaches for the in-situ formation of metal carbene intermediates with structural diversity and unrevealed reactivity. Herein we report a gold-catalyzed cascade protocol for the assembly of polycarbocyclic frameworks in high yields under mild reaction conditions. Mechanistic studies indicate that the unique β-aryl gold-carbene species, generated via gold-promoted 6-endo-dig diazo-yne cyclization, is the key intermediate in this reaction, followed by a [4 + 2]-cycloaddition with external alkenes. In comparison to the well-documented metal carbene cycloadditions, this carbene intermediate serves as a 4-C synthon in a cycloaddition reaction. A variety of elusive π-conjugated polycyclic hydrocarbons (CPHs) with multiple substituents are readily accessible from the initially generated products by a mild oxidation procedure.

Potassium phthalimide-catalysed one-pot multi-component reaction for efficient synthesis of amino-benzochromenes in aqueous media

2014 ◽  
Vol 68 (8) ◽  
Author(s):  
Hamzeh Kiyani ◽  
Fatemeh Ghorbani
Keyword(s):  
Organic Solvent ◽  
Aqueous Media ◽  
Ethyl Cyanoacetate ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Environmentally Benign ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
High Yields

Abstract2-Amino-4-aryl-4H-benzo[h]chromenes and 3-amino-1-aryl-1H-benzo[f]chromenes were prepared by treating cyano-methylene compounds (malononitrile or ethyl cyanoacetate), substituted aromatic aldehydes, and naphtholic compounds in the presence of potassium phthalimide as a green, mild, efficient, and commercially available organocatalyst in aqueous media. The procedure was readily conducted and affords remarkable advantages such as safety, short reaction times, environmentally benign milder reaction conditions, no organic solvent required, and 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.

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