Zr-Catalyzed Microwave Assisted Functionalization of Alkyne and Nitroalkene

2021 ◽  
Vol 6 (4) ◽  
pp. 302-305
Author(s):  
Prakash S. Pawar ◽  
Sandip D. Gorshetwar ◽  
Atul D. Kamble ◽  
Jotiram K. Chavan ◽  
Gurunath G. Chougale ◽  
...  
Keyword(s):  
Aromatic Ring ◽  
Methyl Ketone ◽  
Oxidative Cleavage ◽  
Hydration Reaction ◽  
Terminal Alkyne ◽  
Microwave Assisted ◽  
Excellent Yield

Water and zirconium(IV) as catalyst were found to be effective in the transformation of terminal aromatic alkyne to aromatic methyl ketone in the microwave. This terminal alkyne hydration reaction proceeded in excellent yield with Zr(cp)2Cl2. The reaction was moved efficiently in presence of electron donating or electron withdrawing substituent on aromatic ring. An eco-friendly synthesis of aldehyde by oxidative cleavage of nitroalkene was developed with Zr(cp)2Cl2 catalyst and water in microwave.

scholarly journals Kajian Regiokimia Markovnikov Melalui Mekanisme Reaksi Hidrasi Alkuna Terminal pada Etinilestradiol dengan Katalis FeCl3

2021 ◽  
Vol 6 (1) ◽  
pp. 39
Author(s):  
Hotma Rotua Br. Simbolon ◽  
Rymond Jusuf Rumampuk ◽  
Anderson Arnold Aloanis
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Reaction Mechanism ◽  
Reaction Rate ◽  
Methyl Ketone ◽  
Proton Nuclear Magnetic Resonance ◽  
Hydration Reaction ◽  
Terminal Alkynes ◽  
Terminal Alkyne ◽  
Reaction Products ◽  
Reaction Conditions

The terminal alkynes hydration reaction on 17α-ethynylestradiol (1) with FeCl3 catalyst mediated by dichloromethane aims to determine the reaction products produced and to conduct a Markovnikov regiochemistry study through the proposed reaction mechanism. The reaction conditions were carried out at a temperature of 50oC (48 hours) and 60oC (19 hours), the separation of the reaction properties was carried out using Gravity Column Chromatography, and the reaction products were identification using by Proton Nuclear Magnetic Resonance (1H-NMR). Here we describe the process of the FeCl3 catalyst forming a coordination complex with the terminal alkyne, which is then addition by nucleophilic water following Markovnikov's regiochemistry to finally produce the product of a methyl ketone, 17α-acetylestradiol (6). The catalyst used is a cationic ligand coordinate, where Fe3+ is a Lewis acid and Cl3- acts as a ligand. The dichloromethane solvent used can also increase the reaction rate.

scholarly journals Novel Greener Microwave-Assisted Deprotection Methodology for the 1,3-Dioxolane Ketal of Isatin Using Calix[n]arenes

2022 ◽  
Author(s):  
Lucas Barbosa ◽  
Tiago da Silva ◽  
Michelle Rezende ◽  
Bianca da Silva ◽  
Rodrigo Guzzo ◽  
...  
Keyword(s):  
Aromatic Ring ◽  
Sulfonic Acid ◽  
Microwave Energy ◽  
Protecting Group ◽  
Additional Advantage ◽  
Microwave Assisted ◽  
Combined Use ◽  
Ketone Carbonyl ◽  
First Time ◽  
Hydrolysis Of

In this work, the combined use of p-sulfonic acid-calix[n]arene and microwave energy to hydrolyze the 1,3-dioxolane ketal of isatin was evaluated with excellent results. This is the first time that p-sulfonic acid-calix[n]arene has been used as the catalyst in a ketal hydrolysis reaction and the deprotection of the ketone carbonyl of isatin is reported. The presence of 2.5 mol% of p-sulfonic acid-calix[4,6]arene at 160 ºC resulted in over 96% conversion of this ketal in 10 min, with the additional advantage of using water as a solvent. This catalytic system (aqueous phase containing p-sulfonic acid-calix[4]arene) was reused for five consecutive cycles, with a conversion above 96% maintained. This reusable system is not practicable using p-toluenesulfonic acid and p-hydroxybenzenesulfonic acid as catalysts since both are extracted to the organic phase with the reaction product. The hydrolysis of 1,3-dioxolane ketal of isatins with different substituents (CH3, I, Br, Cl, F, NO2) in the aromatic ring was also evaluated. The protecting group of 5-methyl-isatin was removed with 73% conversion using 2.5 mol% of p-sulfonic acid-calix[4]arene at 160 ºC for 5 min. In contrast, the ketal of 5-nitro-isatin reached 80% conversion using the same conditions after 40 min.

Mercuric Triflate-TMU Catalyzed Hydration of Terminal Alkyne to give Methyl Ketone under Mild Conditions

2002 ◽  
Vol 31 (1) ◽  
pp. 12-13 ◽  
Author(s):  
Mugio Nishizawa ◽  
Mariusz Skwarczynski ◽  
Hiroshi Imagawa ◽  
Takumichi Sugihara
Keyword(s):  
Methyl Ketone ◽  
Terminal Alkyne ◽  
Mild Conditions

Novel binder-free forming of Al2O3 ceramics by microwave-assisted hydration reaction

2008 ◽  
Vol 148 (1-3) ◽  
pp. 221-225 ◽  
Author(s):  
Takashi Shirai ◽  
Masaki Yasuoka ◽  
Koji Watari
Keyword(s):  
Hydration Reaction ◽  
Microwave Assisted ◽  
Binder Free

The metabolism of p-fluorophenylacetic acid by a Pseudomonas sp. II. The degradative pathway

1971 ◽  
Vol 17 (5) ◽  
pp. 645-650 ◽  
Author(s):  
D. B. Harper ◽  
E. R. Blakley
Keyword(s):  
Aromatic Ring ◽  
Hydrogen Fluoride ◽  
Phenylacetic Acid ◽  
Oxidative Cleavage ◽  
Cell Suspensions ◽  
Ring Cleavage ◽  
Pseudomonas Sp ◽  
Partial Reduction ◽  
Degradative Pathway ◽  
Unstable Compound

A Pseudomonas sp. grown on p-fluorophenylacetic acid is adapted to the metabolism of phenylacetic acid, 3-fluoro-3-hexenedioic acid, monofluorosuccinic acid, monofluorofumaric acid, β-ketoadipic acid, and β-hydroxyadipic acid. Cell suspensions catalyze the lactonization of 3-fluoro-3-hexenedioic acid to give 4-carboxymethyl-4-fluorobutanolide. The results suggest that 3-fluoro-3-hexenedioic acid is an intermediate in the degradation of p-fluorophenylacetic acid, and may be metabolized by two alternate pathways, depending on the lactone formed. 4-Carboxymethyl-4-fluorobutanolide may be hydrolyzed to give 3-hydroxy-3-fluoroadipic acid, which spontaneously eliminates hydrogen fluoride to give β-ketoadipic acid. Alternatively, 3-fluoro-3-hexenedioic acid may lactonize to form 4-carboxymethyl-3-fluorobutanolide, which is then hydrolyzed to 3-keto-4-fluoroadipic and cleaved to form acetate and monofluorosuccinic acid. The latter is converted to fluorofumaric acid by fumarase to give 2-fluoromalic acid. This unstable compound decomposes to oxaloacetate and hydrogen fluoride. The mechanism of ring cleavage and the mode of formation of 3-fluoro-3-hexenedioic acid are uncertain but may involve partial reduction of the aromatic ring before oxidative cleavage.

Binder-Free Formation of Alumina Ceramics by a Microwave-Assisted Hydration Reaction

2007 ◽  
Vol 0 (0) ◽  
pp. 070920205701003-???
Author(s):  
Takashi Shirai ◽  
Masaki Yasuoka ◽  
Koji Watari
Keyword(s):  
Hydration Reaction ◽  
Alumina Ceramics ◽  
Microwave Assisted ◽  
Binder Free

ChemInform Abstract: Mercuric Triflate-TMU Catalyzed Hydration of Terminal Alkyne to Give Methyl Ketone under Mild Conditions.

ChemInform ◽  
2010 ◽  
Vol 33 (23) ◽  
pp. no-no
Author(s):  
Mugio Nishizawa ◽  
Mariusz Skwarczynski ◽  
Hiroshi Imagawa ◽  
Takamichi Sugihara
Keyword(s):  
Methyl Ketone ◽  
Terminal Alkyne ◽  
Mild Conditions

Gold nanoparticles supported on layered TiO2–RGO hybrid as an enhanced and recyclable catalyst for microwave-assisted hydration reaction

RSC Advances ◽  
2016 ◽  
Vol 6 (80) ◽  
pp. 76151-76157 ◽  
Author(s):  
Yunfeng Cheng ◽  
Qingshan Zhao ◽  
Yang Li ◽  
Wenchao Peng ◽  
Guoliang Zhang ◽  
...  
Keyword(s):  
Gold Nanoparticles ◽  
Recyclable Catalyst ◽  
Hydration Reaction ◽  
Microwave Assisted

A novel composite (Au–SO42−/TiO2–RGO) is synthesized and serves as an enhanced catalyst for alkyne hydration.

scholarly journals Microwave Assisted Synthesis of 2,4-Diphenyl-4H-chromen-5-one Using ZnCl2/Montmorillonite K-10

2009 ◽  
Vol 6 (1) ◽  
pp. 151-155 ◽  
Author(s):  
Swapnil R. Sarda ◽  
Ujwala S. Maslekar ◽  
Wamanrao N. Jadhav ◽  
Rajendra P. Pawar
Keyword(s):  
Microwave Irradiation ◽  
Carbonyl Compounds ◽  
Microwave Assisted Synthesis ◽  
Microwave Assisted ◽  
Excellent Yield

α, β-Unsaturated carbonyl compounds and 1, 3-cyclohexanedione under microwave irradiation in the presence ZnCl2/montmorillonite K-10 offers the corresponding 2,4-diphenyl-4H-chromen-5-one in excellent yield. Catalyst is recycled and reused for several times

scholarly journals Microwave enhanced synthesis of halogenated derivatives of L-tyrosine labeled with deuterium in aromatic ring

2020 ◽  
Vol 326 (1) ◽  
pp. 857-860
Author(s):  
Małgorzata Pająk
Keyword(s):  
Nmr Spectroscopy ◽  
Aromatic Ring ◽  
Isotope Exchange ◽  
Spectroscopic Data ◽  
Deuterium Incorporation ◽  
H Nmr ◽  
Microwave Assisted ◽  
Acid Catalyzed ◽  
Deuterium Enrichment ◽  
Derivatives Of

Abstract Three halogenated derivatives of L-tyrosine, selectively labeled with deuterium in aromatic ring, i.e., 3′-fluoro-[5′-2H]-, 3′-chloro-[5′-2H]-, and 3′-iodo-[2′,5′-2H2]-L-tyrosine, were synthesized using microwave assisted acid-catalyzed isotope exchange between 3′-fluoro-, 3′-chloro- and 3′-iodo-L-tyrosine and heavy water. The degree of deuterium incorporation was confirmed by 1H NMR spectroscopy. The spectroscopic data indicate that isotope exchange depends on the method of heating and the power of microwaves. The deuterium enrichment of 3′-fluoro-[5′-2H]- and 3′-chloro-[5′-2H]-L-tyrosine amounted to 70% and 60%, respectively, while for 3′-iodo-[2′,5′-2H2]-L-tyrosine this value was about 50% and 95% for the 2′- and 5′-position. The isotopomers were obtained in good chemical yields of 50–70%.

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