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

2013 ◽  
Vol 68 (7) ◽  
pp. 818-822 ◽  
Author(s):  
Rahimeh Hajinasiri ◽  
Sobhan Rezayati

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.

2021 ◽  
Vol 17 ◽  
pp. 2642-2649
Author(s):  
Akhil K Dubey ◽  
Raghunath Chowdhury

An enantioselective 1,4-conjugate addition of nitromethane to β-silyl α,β-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts has been developed. This methodology offers both enantiomers of β-silyl nitroalkanes in good to excellent yields (up to 92%) and enantioselectivities (up to 97.5% ee) under solvent-free conditions at room temperature. Control experiments reveal that the presence of a β-silyl group in the enones is crucial for high reactivity under the optimized reaction conditions.


2017 ◽  
Vol 41 (6) ◽  
pp. 321-324 ◽  
Author(s):  
Mona Arfavi-Safari ◽  
Hossein Anaraki-Ardakani ◽  
Rashid Badri ◽  
Elham Tahanpesar

An efficient and simple protocol for the synthesis of the title compounds is described via a one-pot, three-component reaction of 4-hydroxycoumarin, aryl glyoxals and amides, using SnCl2-SiO2 nanoparticles as a heterogeneous catalyst under solvent-free conditions. The advantages of this synthesis include excellent yields, mild reaction conditions, atom economy, a reusable catalyst and no need for chromatographic separations.


2020 ◽  
Vol 17 ◽  
Author(s):  
Gholamhassan Imanzadeh ◽  
Samira Zolfagharzadeh ◽  
Zahra Soltanzadeh

Abstract:: A number of new N-alkylated derivatives of N-acylhydrazones have been prepared via one pot three-component reaction between hydrazide, aldehyde, and α,β-unsaturated ester using 1,4-diaza-bicyclo[2,2,2]octane (DABCO), as an in-expensive base and tetrabutylammonium bromide (TBAB), an ionic organic salt media, under solvent-free conditions. In the case of 2-hydroxy benzaldehyde, the reaction proceeds with the exclusive formation of the N-alkyl derivative without any concurrent O-alkylation side reaction.


RSC Advances ◽  
2016 ◽  
Vol 6 (45) ◽  
pp. 39452-39459 ◽  
Author(s):  
Nenad Janković ◽  
Jovana Muškinja ◽  
Zoran Ratković ◽  
Zorica Bugarčić ◽  
Branislav Ranković ◽  
...  

A series of novel O-alkyl vanillidene derivatives containing Meldrum's acid scaffold under solvent-free conditions were synthesized.


2021 ◽  
Vol 18 ◽  
Author(s):  
Ali Aminkhani ◽  
Sina Sharifi

: An efficient four-component reaction to synthesize pyrrolo[2,1-a]isoquinolines from malononitrile, aromatic aldehydes, isoquinoline, and cyclohexyl isocyanide under solvent-free conditions is described. In a convenient, simple, and efficient one-pot procedure, the domino Knoevenagel-nucleophilic cycloaddition reaction affords excellent yields of products in less than 1 h.


2012 ◽  
Vol 9 (4) ◽  
pp. 2239-2244 ◽  
Author(s):  
Hossein Anaraki-Ardakani ◽  
Maziar Noei ◽  
Mina Karbalaei-Harofteh ◽  
Shahab Zomorodbakhsh

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.


2013 ◽  
Vol 9 ◽  
pp. 2344-2353 ◽  
Author(s):  
Sudipta Pathak ◽  
Kamalesh Debnath ◽  
Animesh Pramanik

A convenient and efficient methodology for the synthesis of densely substituted pyrrole-fused isocoumarins, which employs solid-supported silica sulfuric acid (SSA) as catalyst, has been developed. When the mixture of ninhydrin adducts of acetylacetone/ethyl acetoacetate and primary amines was heated on the solid surface of SSA under solvent-free conditions, the pyrrole-fused isocoumarins were formed in good yields. This synthetic method has several advantages such as the employment of solvent-free reaction conditions without the use of any toxic reagents and metal catalysts, the ease of product isolation, the use of a recyclable catalyst, the low cost, the easy availability of the starting materials, and the excellent yields of products.


Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 744-754
Author(s):  
Yoona Song ◽  
Soyun Lee ◽  
Palash Dutta ◽  
Jae-Sang Ryu

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.


2019 ◽  
Vol 31 (6) ◽  
pp. 1357-1361 ◽  
Author(s):  
NARENDRA R. KAMBLE ◽  
VINOD T. KAMBLE

A combinatorial library of benzylpyrazolyl coumarin derivatives have been synthesized by a green one-pot four-component reaction between aryl hydrazine/hydrazine hydrate (1), ethyl acetoacetate (2), aromatic aldehydes (3) and 4-hydroxycoumarin (4) catalyzed by niobium pentachloride with silver salt under solvent-free conditions has been developed. Experimental simplicity, simple work-up procedure and solvent-free reaction condition at room temperature are important features of the present protocol.


2020 ◽  
Vol 50 (10) ◽  
pp. 1545-1560 ◽  
Author(s):  
Gurpreet Kaur ◽  
Mussarat Shamim ◽  
Vaishali Bhardwaj ◽  
Vivek Kumar Gupta ◽  
Bubun Banerjee

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