A Copper(I)-Mediated Tandem Three-Component Synthesis of 5-Allyl-1,2,3-triazoles

A copper(I)-mediated tandem three-component reaction using alkynes, azides, allyl iodides, CuI and NaNH2 is developed. The reactions proceed smoothly at room temperature to afford 5-allyl-1,2,3-triazoles, which can be further converted into 1,2,3-triazole-fused tricyclic scaffolds. This method features an efficient one-pot cascade route using commercial alkynes and affords the corresponding 5-allyl-1,2,3-triazoles with high yields and good selectivity under mild reaction conditions.

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

Letters in Organic Chemistry ◽

10.2174/1570178617999201020215852 ◽

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 ◽

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.

A Facile Synthesis of Polysubstituted Pyrroles by One-Pot Three-Component Reaction

E-Journal of Chemistry ◽

10.1155/2012/915861 ◽

2012 ◽

Vol 9 (4) ◽

pp. 2239-2244 ◽

Cited By ~ 5

Author(s):

Hossein Anaraki-Ardakani ◽

Maziar Noei ◽

Mina Karbalaei-Harofteh ◽

Shahab Zomorodbakhsh

Keyword(s):

Room Temperature ◽

Facile Synthesis ◽

One Pot ◽

Pyrrole Derivatives ◽

Dialkyl Acetylenedicarboxylates ◽

One Pot Synthesis ◽

High Yields ◽

Neutral Conditions

A new and efficient one-pot synthesis of polysubstituted pyrrole derivatives by three-component reaction between dialkyl acetylenedicarboxylates, triphenylphosphine, 2-aminopyridin derivatives in the presence of arylglyoxals is described. The reactions were performed in dichloromethane at room temperature and neutral conditions and afforded high yields of products.

Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.15.85 ◽

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 ◽

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.

One-pot, three-component synthesis of pyrrolo[2,3-d]pyrimidine derivatives

Journal of the Mexican Chemical Society ◽

10.29356/jmcs.v62i1.340 ◽

2018 ◽

Vol 62 (1) ◽

Author(s):

Jabbar Khalafy ◽

Ramin Javahershenas

Keyword(s):

Simple Procedure ◽

Reaction Times ◽

Pyrimidine Derivatives ◽

Reaction Conditions ◽

One Pot ◽

General Applicability ◽

Green Approach ◽

High Yields ◽

Work Up

A green approach for the synthesis of polyfunctionalized pyrrolo[2,3-d]pyrimidine derivatives was successfully achieved by a one-pot, three-component reaction of arylglyoxals, 6-amino-1,3-dimethyluracil and barbituric acid derivatives in the presence of tetra-n-butylammonium bromide (TBAB) (5 mol%) as the catalyst in ethanol at 50 °C. This protocol has many advantages such as high yields (73-95%), green and simple procedure, short reaction times, easy work-up, mild reaction conditions and general applicability.

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 ◽

10.1055/s-0039-1690768 ◽

2019 ◽

Vol 31 (03) ◽

pp. 267-271 ◽

Cited By ~ 2

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 ◽

Relative Stereochemistry ◽

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.

An Efficient Isocyanide-Based Three-Component Synthesis of Novel Ketenimines

JOURNAL OF ADVANCES IN CHEMISTRY ◽

10.24297/jac.v10i3.2286 ◽

2014 ◽

Vol 10 (3) ◽

pp. 2363-2368

Author(s):

Hamideh Emtiazi ◽

Mohammad Ali Amrollahi

Keyword(s):

Room Temperature ◽

Simple Procedure ◽

Reaction Times ◽

Dimethyl Acetylenedicarboxylate ◽

One Pot ◽

This study provides a description of an efficient and simple procedure for the synthesis of dimethyl 2-(9-aryl)-3,3,6,6-tetramethyl-1,8-diox-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)-3-((cyclohexylimino)methylene)succinate via a one-pot three-component reaction of cyclohexyl isocyanide, dimethyl acetylenedicarboxylate and hexahydroacridine-1,8(2H,5H)-dionesin CH2Cl2 at room temperature. Short reaction times, good to high yields and the novelty are the remarkable advantages of this work.

Catalyst-Free Three-Component Synthesis of Spirobenzimidazolidines Bearing an Indole Scaffold

Synlett ◽

10.1055/s-0037-1609950 ◽

2018 ◽

Vol 29 (17) ◽

pp. 2301-2305 ◽

Cited By ~ 3

Author(s):

F. Moghaddam ◽

A. Moafi ◽

Z. Zamani ◽

M. Daneshfar

Keyword(s):

Reaction Times ◽

Reaction Conditions ◽

One Pot ◽

Efficient Catalyst ◽

Catalyst Free ◽

New Family ◽

High Yields ◽

First Time ◽

Derivatives Of

An efficient catalyst-free one-pot three-component reaction was developed for the synthesis of a new family of N- and S-containing spirocyclic compounds. Various derivatives of spirobenzimidazolidine containing an indole scaffold were synthesized for the first time in a modestly toxic solvent and under mild reaction conditions. The reaction times were of the order of several minutes, and all the products were obtained in moderate to high yields (overall yields 58–80%).

Two Efficient One-Pot Approaches for Regioselective Synthesis of New 3-Arylpyridazino[4,3-c]quinolin-5(6H)-ones

Australian Journal of Chemistry ◽

10.1071/ch15029 ◽

2015 ◽

Vol 68 (10) ◽

pp. 1529 ◽

Cited By ~ 11

Author(s):

Mehdi Rimaz

Keyword(s):

Hydrazine Hydrate ◽

Regioselective Synthesis ◽

Reaction Conditions ◽

One Pot ◽

One Pot Synthesis ◽

The One ◽

High Yields ◽

Arylglyoxal Monohydrates ◽

Operational Simplicity

Two efficient regioselective approaches for the one-pot synthesis of 3-arylpyridazino[4,3-c]quinolin-5(6H)-one derivatives are reported, by the three-component reaction of arylglyoxal monohydrates, quinoline-2,4-diol, and hydrazinium dihydrochloride or hydrazine hydrate in ethanol and pyridine. In ethanol, the reactions were catalyzed by 1,4-diazobicyclo[2,2,2]octane. The features of both procedures are high regioselectivity, mild reaction conditions, good to high yields, and operational simplicity.

Solvent-free Synthesis of 1,2-Disubstituted Derivatives of 1,2- Dihydroisoquinoline, 1,2-Dihydroquinoline and 1,2-Dihydropyridine

Zeitschrift für Naturforschung B ◽

10.5560/znb.2013-3095 ◽

2013 ◽

Vol 68 (7) ◽

pp. 818-822 ◽

Cited By ~ 8

Author(s):

Rahimeh Hajinasiri ◽

Sobhan Rezayati

Keyword(s):

Room Temperature ◽

Solvent Free ◽

Reaction Conditions ◽

One Pot ◽

Efficient Approach ◽

Dialkyl Acetylenedicarboxylates ◽

Solvent Free Conditions ◽

Derivatives Of ◽

Solvent Free Synthesis

A one-pot and efficient approach to the synthesis of dialkyl 2-[1-[(alkoxycarbonyl)anilino]-2(1H)- (isoquinolin-2-yl) (or -quinolin-1-yl or -pyridin-1-yl)]-2-butenedioates is described. This method involves a three-component reaction between isoquinoline, quinoline or pyridine, dialkyl acetylenedicarboxylates and N-phenylcarbamates under solvent-free conditions, without using any catalyst and at room temperature. The mild reaction conditions and good yields of the products exhibit the synthetic advantage of this method.

One-pot Synthesis of Pyrazolone Sulfones by Iodine-catalyzed Sulfenylation of Pyrazolones with Aryl Sulfonyl Hydrazides Followed by Oxidation in Water

Current Organic Synthesis ◽

10.2174/1570179414666171020113745 ◽

2018 ◽

Vol 15 (3) ◽

pp. 380-387

Author(s):

Xia Zhao ◽

Xiaoyu Lu ◽

Lipeng Zhang ◽

Tianjiao Li ◽

Kui Lu

Keyword(s):

Double Bond ◽

Efficient Method ◽

Room Temperature ◽

Sulfonyl Chloride ◽

Antibacterial Activities ◽

Oxidation Reactions ◽

Reaction Conditions ◽

One Pot ◽

X Ray ◽

Amide Form

Aim and Objective: Pyrazolone sulfones have been reported to exhibit herbicidal and antibacterial activities. In spite of their good bioactivities, only a few methods have been developed to prepare pyrazolone sulfones. However, the substrate scope of these methods is limited. Moreover, the direct sulfonylation of pyrazolone by aryl sulfonyl chloride failed to give pyrazolone sulfones. Thus, developing a more efficient method to synthesize pyrazolone sulfones is very important. Materials and Method: Pyrazolone, aryl sulphonyl hydrazide, iodine, p-toluenesulphonic acid and water were mixed in a sealed tube, which was heated to 100°C for 12 hours. The mixture was cooled to 0°C and m-CPBA was added in batches. The mixture was allowed to stir for 30 min at room temperature. The crude product was purified by silica gel column chromatography to afford sulfuryl pyrazolone. Results: In all cases, the sulfenylation products were formed smoothly under the optimized reaction conditions, and were then oxidized to the corresponding sulfones in good yields by 3-chloroperoxybenzoic acid (m-CPBA) in water. Single crystal X-ray analysis of pyrazolone sulfone 4aa showed that the major tautomer of pyrazolone sulfones was the amide form instead of the enol form observed for pyrazolone thioethers. Moreover, the C=N double bond isomerized to form an α,β-unsaturated C=C double bond. Conclusion: An efficient method to synthesize pyrazolone thioethers by iodine-catalyzed sulfenylation of pyrazolones with aryl sulfonyl hydrazides in water was developed. Moreover, this method was employed to synthesize pyrazolone sulfones in one-pot by subsequent sulfenylation and oxidation reactions.