Naturally Occurring Organic Acid-catalyzed Facile Diastereoselective Synthesis of Biologically Active (E)-3-(arylimino)indolin-2-one Derivatives in Water at Room Temperature

2019 ◽  
Vol 23 (16) ◽  
pp. 1778-1788 ◽  
Author(s):  
Gurpreet Kaur ◽  
Arvind Singh ◽  
Kiran Bala ◽  
Mamta Devi ◽  
Anjana Kumari ◽  
...  
Keyword(s):  
Room Temperature ◽  
Biologically Active ◽  
Environmentally Benign ◽  
Diastereoselective Synthesis ◽  
Substituted Anilines ◽  
Reaction Conditions ◽  
Naturally Occurring ◽  
Acid Catalyzed ◽  
Reaction Media ◽  
Column Chromatographic

A simple, straightforward and efficient method has been developed for the synthesis of (E)-3-(arylimino)indolin-2-one derivatives and (E)-2-((4-methoxyphenyl)imino)- acenaphthylen-1(2H)-one. The synthesis of these biologically-significant scaffolds was achieved from the reactions of various substituted anilines and isatins or acenaphthaquinone, respectively, using commercially available, environmentally benign and naturally occurring organic acids such as mandelic acid or itaconic acid as catalyst in aqueous medium at room temperature. Mild reaction conditions, energy efficiency, good to excellent yields, environmentally benign conditions, easy isolation of products, no need of column chromatographic separation and the reusability of reaction media are some of the significant features of the present protocol.

A General Method for the Synthesis of 11H-indeno[1,2-b]quinoxalin-11-ones and 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one Derivatives using Mandelic Acid as an Efficient Organo-catalyst at Room Temperature

2021 ◽  
Vol 08 ◽  
Author(s):  
Aditi Sharma ◽  
Gurpreet Kaur ◽  
Diksha Singh ◽  
Vivek Kumar Gupta ◽  
Bubun Banerjee
Keyword(s):  
Mandelic Acid ◽  
Room Temperature ◽  
Aqueous Ethanol ◽  
Low Cost ◽  
Catalytic Amount ◽  
Reaction Conditions ◽  
Metal Free ◽  
Naturally Occurring ◽  
Column Chromatographic ◽  
General Method

Aims: Synthesis of 11H-indeno[1,2-b]quinoxalin-11-ones as well as 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives under greener conditions. Background: Quinoxaline and related skeletons are very common in naturally occurring bioactive compounds. Objective: Design a facile, green and organo-catalyzed method for the synthesis of 11H-indeno[1,2-b]quinoxalin-11-ones as well as 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives. Methods: Both the scaffolds were synthesized via the condensation of ninhydrin and o-phenylenediamines or pyridine-2,3-diamines respectively by using a catalytic amount of mandelic acid as an efficient, commercially available, low cost, organo-catalyst in aqueous ethanol at room temperature. Results: Mild reaction conditions, use of metal-free organocatalyst, non-toxic solvent, ambient temperature, and no column chromatographic separation are some of the notable advantages of our developed protocol. Conclusion: In conclusion, we have developed a simple, mild, facile and efficient method for the synthesis of structurally diverse 11H-indeno[1,2-b]quinoxalin-11-one derivatives via the condensation reactions of ninhydrin and various substituted benzene-1,2-diamines using a catalytic amount of mandelic acid as a commercially available metal-free organo-catalyst in aqueous ethanol at room temperature. Under the same optimized reaction conditions, synthesis of 6H-indeno[1,2-b]pyrido[3,2-e]pyrazin-6-one derivatives was also accomplished with excellent yields by using pyridine-2,3-diamines instead of o-phenylenediamine.

Mandelic acid: An efficient organo-catalyst for the synthesis of 3-substituted- 3-hydroxy-indolin-2-ones and related derivatives in aqueous ethanol at room temperature

2020 ◽  
Vol 07 ◽  
Author(s):  
Gurpreet Kaur ◽  
Rajat Kumar ◽  
Shivam Saroch ◽  
Vivek Kumar Gupta ◽  
Bubun Banerjee
Keyword(s):  
Mandelic Acid ◽  
Room Temperature ◽  
Aqueous Ethanol ◽  
Catalytic Amount ◽  
Environmentally Benign ◽  
Scale Production ◽  
Indole Derivatives ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Naturally Occurring

Background: Indoles and various indolyl derivates are very common in naturally occurring biological active compounds. Many methods are being developed for the synthesis of various bioactive indole derivatives. Objective: Synthesis of biologically promising structurally diverse indole derivatives under mild and environmentally benign conditions. Methods: Synthesis of 3-hydroxy-3-(5-(trifluoromethoxy)-1H-indol-3-yl)indolin-2-one was achieved by the reaction of equimolar mixture of isatin and 3-(trifluoromethoxy)-1H-indol using 20 mol% of mandelic acid as catalyst in aqueous ethanol at room temperature. Under the same optimized reaction conditions, synthesis of 3-(3-hydroxy-2-oxoindolin-3- yl)chroman-2,4-diones was accomplished via the reactions of substituted isatins and 4-hydroxycoumarin. On the other hand, 2-hydroxy-2-(indol-3-yl)-indene-1,3-diones and 10-hydroxy-10-(5-methoxy-1H-indol-3-yl)phenanthren-9(10H)-one were synthesized from the reactions of indoles and ninhydrin or 9,10-phenanthrenequinone respectively using the same 20 mol% of mandelic acid as an efficient organo-catalyst in aqueous ethanol at room temperature. Results: Mild, safe and clean reaction profiles, energy efficiency, high atom-economy, use of naturally occurring nontoxic organo-catalyst, easy isolation procedure by avoiding column chromatographic purification and gram scale production are some the major advantages of this developed protocol. Conclusion: A simple, straightforward and eco-friendly protocol has been developed for the efficient synthesis of biologically promising novel 3-hydroxy-3-(5-(trifluoromethoxy)-1H-indol-3-yl)indolin-2-one, 3-(3-hydroxy-2- oxoindolin-3-yl)chroman-2,4-diones, 2-hydroxy-2-(indol-3-yl)-indene-1,3-diones and 10-hydroxy-10-(5-methoxy-1Hindol-3-yl)phenanthren-9(10H)-one using a catalytic amount of mandelic acid in aqueous ethanol at room temperature.

scholarly journals Synthesis of Pyrazolo-Fused 4-Azafluorenones in an Ionic Liquid. Mechanistic Insights by Joint Studies Using DFT Analysis and Mass Spectrometry

Catalysts ◽  
2019 ◽  
Vol 9 (10) ◽  
pp. 820
Author(s):  
Efraín Polo ◽  
Valentina Arce-Parada ◽  
Xaviera A. López-Cortés ◽  
Jesús Sánchez-Márquez ◽  
Alejandro Morales-Bayuelo ◽  
...  
Keyword(s):  
Ionic Liquid ◽  
Density Functional ◽  
Room Temperature ◽  
Theoretical Study ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Conceptual Density Functional Theory ◽  
Functional Theory ◽  
Three Component Reaction ◽  
Work Up

A series of pyrazolo-fused 4-azafluorenones (indeno[1,2-b]pyrazolo[4,3-e]pyridines, IPP) were synthesized via the three-component reaction between arylaldehydes, 3-methyl-1H-pyrazol-5-amine and 1,3-indanedione in an ionic liquid as a catalyst at room temperature. The applied synthetic route has the advantages of easy work-up under mild reaction conditions presenting moderate yields and an environmentally benign procedure. A theoretical study based on conceptual-density functional theory has been done, bond reactivity indices have been calculated and an electrophilic and nucleophilic character of localized orbitals has been determined to analyze the possible electronic mechanisms.

Efficient Copper-Catalyzed Synthesis of Substituted Pyrazoles at Room Temperature

Synlett ◽  
2018 ◽  
Vol 29 (20) ◽  
pp. 2689-2692 ◽  
Author(s):  
Haifeng Wang ◽  
Xiangli Sun ◽  
Shuangling Zhang ◽  
Guanglu Liu ◽  
Chunjie Wang ◽  
...  
Keyword(s):  
Reaction Time ◽  
Catalytic System ◽  
Efficient Method ◽  
Room Temperature ◽  
Copper Catalyst ◽  
Condensation Reaction ◽  
Reaction Conditions ◽  
Short Reaction Time ◽  
Acid Catalyzed ◽  
Substituted Pyrazoles

An efficient method for the synthesis of pyrazoles through a copper-catalyzed condensation reaction has been developed. The new catalytic system not only maintained a broad substrate scope but was also active under acid-free reaction conditions, overcoming the conventional requirement for an acid-catalyzed system. Furthermore, the copper catalyst enabled this reaction to be performed at room temperature and in a short reaction time.

scholarly journals ZnO-beta zeolite mediated simple and efficient method for the one-pot synthesis of quinoxaline derivatives at room temperature

2010 ◽  
Vol 8 (2) ◽  
pp. 320-325 ◽  
Author(s):  
Santosh Katkar ◽  
Pravinkumar Mohite ◽  
Lakshman Gadekar ◽  
Balasaheb Arbad ◽  
Machhindra Lande
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Environmentally Benign ◽  
Beta Zeolite ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Quinoxaline Derivatives ◽  
The One ◽  
Work Up

AbstractA rapid and an efficient one-pot method for the synthesis of quinoxalines catalysed by ZnO-beta zeolite at room temperature is described. This environmentally benign method provides several advantages over methods that are currently employed such as a simple work-up, mild reaction conditions, good to excellent yields, and a process to recover and reuse the catalyst for several cycles with consistent activity.

scholarly journals Chiral Tetrahydropyridines via FeCl3-Catalyzed Carbonyl-Olefin Metathesis

2019 ◽  
Author(s):  
Katie Rykaczewski ◽  
Emilia J. Groso ◽  
Hannah L. Vonesh ◽  
Mario Gaviria ◽  
Alistair D. Richardson ◽  
...  
Keyword(s):  
Amino Acids ◽  
Lewis Acid ◽  
Olefin Metathesis ◽  
Unnatural Amino Acids ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Reaction Proceeds ◽  
Acid Catalyzed

<div> <div> <p>Herein, we describe the application of Lewis acid-catalyzed carbonyl-olefin metathesis towards the synthesis of chiral, substituted tetrahydropyridines from commercially available amino acids as chiral pool reagents. This strategy relies on FeCl<sub>3</sub> as an inexpensive and environmentally benign catalyst and enables access to a variety of substituted tetrahydropyridines under mild reaction conditions. The reaction proceeds with complete stereoretention and is viable for a variety of natural and unnatural amino acids to provide the corresponding tetrahydropyridines in up to 99% yield.</p> </div> </div> <br>

Ionic liquid Mediated Synthesis of Schiff bases bearing thiazole and indole moieties

2020 ◽  
Vol 17 ◽  
Author(s):  
Dhanaji Jawale ◽  
Devendra Wagare ◽  
Dinesh Lingampalle ◽  
Prashant Netankar
Keyword(s):  
Ionic Liquid ◽  
Schiff Bases ◽  
Heterocyclic Compounds ◽  
Ammonium Acetate ◽  
Biologically Active ◽  
Environmentally Benign ◽  
Melting Points ◽  
Peg 400 ◽  
Reaction Media ◽  
Layer Chromatography

Aims: Ionic liquid Mediated Synthesis of Schiff bases bearing thiazole and indole moieties. Background: Synthesis of biologically active heterocyclic compounds using environmentally benign method. Materials and Methods: A mixture of amino thiazoles (3a-i) (20 mmol), indole-3-carboxyaldehyde (4) (20 mmol) and ionic liquid (80 mmol) was stirred in ethanol (30 mL) at r.t. The progress of the reaction was monitored by thin layer chromatography. After stirring the reaction mass for 2h the solid mass appeared in the reaction was filtered and crystalized using ethanol. The melting points and the yields of the derivatives are recorded in the Table 2. The filtrate was distilled and residue, ionic liquid was reused for the further reactions of the same batch and noted that it gave moderate to good yields of the products. Results and Discussion: Thus a convenient synthetic protocol for the synthesis of new Schiff bases, N-(4-(3-(4-(4- phenylthiazol-2-ylimino) methyl) phenoxy) propoxy) benzylidene)-4-phenylthiazol-2-amines, (8a-i) and N-((1H-indol-3-yl) methylene)-4-phenylthiazol-2-amines,(5a-i) has been developed by separately allowing the interactions of bis aldehyde (7) and 3-formyl indole (4) with amino thiazoles, (3a-i) in 2-hydroxy ethyl ammonium acetate, an ionic liquid, at r. t. (Scheme 1). Acetophenones, (1a-i) and thiourea were allowed to condense in PEG-400 in the presence of NBS and obtained better yields of aminothiazoles, (3a-i). Amino thiazoles when separately condensed with indole-3-carboxyaldehyde (4) and bis aldehyde (7) in ionic liquid, 2-hydroxy ethyl ammonium acetate (9) gave respective new azomethines, N-((1H-indol-3-yl) methylene)-4-phenylthiazol-2-amines, (5a-i) and N-(4-(3-(4-(4-phenylthiazol-2-ylimino) methyl) phenoxy) propoxy) benzylidene)-4-phenylthiazol-2-amine, (8a-i), respectively. Conclusion: We have synthesized new Schiff bases at r.t. using freshly prepared ionic liquid as medium. This method useful for the preparation of library of Schiff bases. The starting, material required for the synthesis of the Schiff bases, amino thiazoles have been prepared using green reaction media.

scholarly journals Chiral Tetrahydropyridines via FeCl3-Catalyzed Carbonyl-Olefin Metathesis

2019 ◽  
Author(s):  
Katie Rykaczewski ◽  
Emilia J. Groso ◽  
Hannah L. Vonesh ◽  
Mario Gaviria ◽  
Alistair D. Richardson ◽  
...  
Keyword(s):  
Amino Acids ◽  
Lewis Acid ◽  
Olefin Metathesis ◽  
Unnatural Amino Acids ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Reaction Proceeds ◽  
Acid Catalyzed

<div> <div> <p>Herein, we describe the application of Lewis acid-catalyzed carbonyl-olefin metathesis towards the synthesis of chiral, substituted tetrahydropyridines from commercially available amino acids as chiral pool reagents. This strategy relies on FeCl<sub>3</sub> as an inexpensive and environmentally benign catalyst and enables access to a variety of substituted tetrahydropyridines under mild reaction conditions. The reaction proceeds with complete stereoretention and is viable for a variety of natural and unnatural amino acids to provide the corresponding tetrahydropyridines in up to 99% yield.</p> </div> </div> <br>

Regio- and Stereoselective Synthesis of a Novel Family of Unsaturated Compounds with the S–Se Bond and Their Cyclization to 2,3-Dihydro-1,4-thiaselenines

Synthesis ◽  
2019 ◽  
Vol 51 (08) ◽  
pp. 1832-1840 ◽  
Author(s):  
Svetlana Amosova ◽  
Andrey Filippov ◽  
Vladimir Potapov ◽  
Maxim Penzik ◽  
Nataliya Makhaeva ◽  
...  
Keyword(s):  
Ring Opening ◽  
Room Temperature ◽  
Stereoselective Synthesis ◽  
Reaction Times ◽  
Nucleophilic Attack ◽  
Selenium Atom ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Ring Opening Reaction ◽  
Acid Catalyzed

Regio- and stereoselective ring-opening reaction of 2-bromomethyl-1,3-thiaselenole with thiols proceeded as nucleophilic attack at the selenium atom of seleniranium intermediate affording unsaturated selanyl sulfides, (Z)-CH2=CHSCH=CHSeSR, in up to 93% yield. Dithiols were involved in this reaction giving symmetrical polyunsaturated compounds with two S–Se bonds in 70–75% yields. Efficient synthesis of 2-(organylsulfanyl)-2,3-dihydro-1,4-thiaselenines in 69–96% yields was developed by the acid-catalyzed cyclization of the unsaturated selanyl sulfides. Mild reaction conditions (room temperature) and short reaction times are important features of this methodology.

Lewis Acid Catalyzed Regio- and Diastereoselective Synthesis of Spiroisoxazolines via One-Pot Sequential Knoevenagel Condensation/1,3-Dipolar Cycloaddition Reaction

Synthesis ◽  
2019 ◽  
Vol 51 (07) ◽  
pp. 1669-1679 ◽  
Author(s):  
Ayoob Bazgir ◽  
Hossein Yazdani
Keyword(s):  
Knoevenagel Condensation ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Coupling Reactions ◽  
Diastereoselective Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Ch Acids ◽  
Acid Catalyzed ◽  
Metal Catalyzed

A ZnCl2-catalyzed regio- and diastereoselective one-pot sequential Knoevenagel condensation/1,3-dipolar cycloaddition reaction of CH acids (oxindole, 1,3-indandione, and 3H-pyrazol-3-one), aldehydes, and dibromoformaldoxime has been established. The method allows the synthesis of diversely functionalized spiroisoxazolines in good isolated yields under mild reaction conditions. Moreover, the preparation of spiroindene-isoxazole-1,3-diones containing benzoimidazole or benzothiazole moieties as new ligands for the metal-catalyzed coupling reactions and C–H activation is demonstrated.

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