Three‐Component, One‐Pot Synthesis of Pyrazolo[3,4‐b]pyridine Derivatives in Aqueous Media
TL;DR: In this article, a three-component reaction of aromatic aldehydes, malononitrile, and 5-amino-3-methyl-1-phenylpyrazole using sodium 1-dodecanesulfonic (SDS) as catalyst in aqueous media is described.
About: This article is published in Synthetic Communications.The article was published on 2008-04-24. It has received 22 citations till now. The article focuses on the topics: Malononitrile & Pyridine.
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386 citations
TL;DR: An efficient one-pot synthesis of spirooxindole derivatives by three-component reaction of isatins, malononitrile and 1,3-dicarbonyl compounds in water in the presence of l-proline is reported.
Abstract: An efficient one-pot synthesis of spirooxindole derivatives by three-component reaction of isatins, malononitrile (cyanoacetic ester) and 1,3-dicarbonyl compounds in water in the presence of l-proline is reported This new protocol has the advantages of environmental friendliness, higher yields, shorter reaction times, low cost, and convenient operation
245 citations
TL;DR: A novel and efficient one-pot synthesis of spiro[indoline-3, 4'-pyrazolo[3,4-b]quinoline]dione, spiro,[furo[3-4-e]pyrazole]dion, and spiro [indeno[2,1-e], pyridine-4,3'-indoline]-dione derivatives via three-component reaction of isatin, 5-amino-3-methylpy
Abstract: A novel and efficient one-pot synthesis of spiro[indoline-3,4′-pyrazolo[3,4-b]quinoline]dione, spiro[furo[3,4-e]pyrazolo[3,4-b]pyridine-4,3′-indoline]dione, and spiro[indeno[2,1-e]pyrazolo[3,4-b]pyridine-4,3′-indoline]dione derivatives via three-component reaction of isatin, 5-amino-3-methylpyrazole, and 1,3-dicarbonyl compounds in aqueous medium is described. The advantages of this method include high efficiency, mild reaction conditions, convenient operation, and environmentally benign conditions.
143 citations
TL;DR: In this article, a nanostructured melamine-based organo solid acid with phosphorus acid tags was designed, synthesized and fully characterized, and the catalytic activity of the resulted melamine hexakis(methylene)hexakis(phosphonic acid) (MHMHPA) as a heterogeneous catalyst was also investigated via an one-pot reaction between cyanoacetylindole, 3-methyl-1-phenyl-1H-pyrazol-5-amine, and an aromatic aldehyde.
37 citations
TL;DR: In this paper, a mesoporous metal-organic framework (MOF) with sulfonic acid tags was synthesized, which was used for the synthesis of dicyanomethylene pyridine derivatives.
Abstract: A metal–organic framework (MOF) with sulfonic acid tags as a novel mesoporous catalyst was synthesized. The precursor of Zr-UiO-66-PDC was synthesized both via chemical and electrochemical methods. Then, zirconium-based mesoporous metal–organic framework [Zr-UiO-66-PDC-SO3H]Cl was prepared by reaction of Zr-UiO-66-PDC and SO3HCl. The structure of [Zr-UiO-66-PDC-SO3H]Cl was confirmed by FT-IR, PXRD, FE-SEM, TEM, BET, EDX, and Mapping analysis. This mesoporous [Zr-UiO-66-PDC-SO3H]Cl was successfully applied for the synthesis of dicyanomethylene pyridine derivatives via condensation of various aldehyde, 2-aminoprop-1-ene-1,1,3-tricarbonitrile and malononitrile. At the electrochemical section, a green electrochemical method has successfully employed for rapid synthesis of the zirconium-based mesoporous metal–organic framework UiO-66-PDC at room temperature and atmospheric pressure. The synthesized UiO-66-PDC has a uniform cauliflower-like structure with a 13.5 nm mean pore diameter and 1081.6 m2 g−1 surface area. The described catalyst [Zr-UiO-66-PDC-SO3H]Cl was also employed for the convergent paired electrochemical synthesis of dihydropyridine derivatives as an environmentally friendly technique under constant current at 1.0 mA cm−2 in an undivided cell. The proposed method proceeds with moderate to good yields for the model via a cooperative vinylogous anomeric based oxidation.
25 citations
References
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TL;DR: Reaction of R,â-Unsaturated Carbonyl Compounds 3127: Reaction of R-UnSaturated Carbonies 3127 7.1.6.
Abstract: 4.2.8. Reductive Coupling 3109 5. Reaction of Aromatic Compounds 3110 5.1. Electrophilic Substitutions 3110 5.2. Radical Substitution 3111 5.3. Oxidative Coupling 3111 5.4. Photochemical Reactions 3111 6. Reaction of Carbonyl Compounds 3111 6.1. Nucleophilic Additions 3111 6.1.1. Allylation 3111 6.1.2. Propargylation 3120 6.1.3. Benzylation 3121 6.1.4. Arylation/Vinylation 3121 6.1.5. Alkynylation 3121 6.1.6. Alkylation 3121 6.1.7. Reformatsky-Type Reaction 3122 6.1.8. Direct Aldol Reaction 3122 6.1.9. Mukaiyama Aldol Reaction 3124 6.1.10. Hydrogen Cyanide Addition 3125 6.2. Pinacol Coupling 3126 6.3. Wittig Reactions 3126 7. Reaction of R,â-Unsaturated Carbonyl Compounds 3127
2,031 citations
TL;DR: In the last decade, there has been increasing recognition that organic reactions carried out in aqueous media may offer advantages over those occurring in organic solvents as discussed by the authors, which is the essence of organic synthesis.
Abstract: Carbon-carbon bond formation is the essence of organic synthesis. Although the well-known Kolbe synthesis was discovered in 1849Ia (the first observation wasmadein 1834byFaraday),'bformorethanacentury, carbon-carbon bond formation in aqueous media has been limited mainly to electrochemical processes and aldol condensation reactions. This is in contrast to the many enzymatic processes that by necessity must occur in an aqueous environment. In the last decade, there has been increasing recognition that organic reactions carried out in aqueous media may offer advantages over those occurring in organic solvents. For example, protection and deprotection processes in organic synthesis can possibly be simplified. This review will survey this area, concentrating mainly on the last decade. The review is organized into three main portions: nonorganometallic reactions, organometallic reactions, and transition-metal-catalyzed organic reactions in aqueous media. The conventional aldol-type and related reactions, stabilized carbanion alkylation reactions, electrochemical reactions as well as bioorganic reactions involving aqueous media and leading to carbon-carbon bond formation will not be included.
1,142 citations
"Three‐Component, One‐Pot Synthesis ..." refers background in this paper
...Recently, there has been increasing recognition that water is an attractive medium for many organic reactions.([9]) Based on our previous studies on the use of water as a solvent for carrying out carbon–carbon bond-forming reactions under phase-transmitting catalyst,([10]) here we like to report onepot synthesis of pyrazolo[3,4-b]pyridine derivatives by three-component reaction in aqueous media (Scheme 1)....
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TL;DR: In this paper, the chemistry and biological properties of pyrazolopyrimidines and pyrazolo[3,4-d]pyrimidine were discussed. But the authors focused on theoretical methods, spectra, and tautomerism.
Abstract: Publisher Summary The interesting biological activities reported for pyrazolopyrimidines have stimulated chemists to develop the chemistry of this class of compounds. This chapter appears to be the first survey of the chemistry and biological activity of this class of compounds. Condensation of β-keto esters with 3( 5)-aminopyrazoles has been used extensively to synthesize pyrazolo[ 1,5-a]pyrimidines. Theoretically, two isomeric pyrazolo[ 1,5-a] pyrimidines can be produced. The parent pyrazolo pyrimidine has been synthesized via cyclocondensation of 1-unsubstituted 3(5)-aminopyrazoles (12) with malonodialdehyde tetramethylacetate. This approach was used to synthesize several substituted pyrazolo pyrimidines. 3- Oxoalkanonitriles and their functional derivatives condense readily with 12 to yield 7-aminopyrazolo. And benzoylacetonitrile and its p-chlorophenylazo and acetylbenzyl cyanide derivatives react with β-cyanoethylhydrazine (74) to yield pyrazolo pyrimidines formed via l-β-cyanoethyl-5-aminopyrazole intermediates. The chapter also discusses chemical properties of pyrazolo[ 1,5-a]pyrimidines and pyrazolo[3,4-d]pyrimldines and elaborates on theoretical methods, spectra, and tautomerism.
112 citations
TL;DR: In this paper, a triethylbenzylammonium chloride (TEBA) was used as a catalyst in aqueous media for a three-component reaction of aromatic aldehydes, malononitrile, and 3-methyl-phenyl-2-pyrazolin.
77 citations
"Three‐Component, One‐Pot Synthesis ..." refers methods in this paper
...9 Based on our previous studies on the use of water as a solvent for carrying out carbon–carbon bond‐forming reactions under phase‐transmitting catalyst, 10 here we like to report one‐pot synthesis of pyrazolo[3,4‐ b ]pyridine derivatives by three‐component reaction in aqueous media ( Scheme 1 )....
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66 citations