One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling–intramolecular cyclization

2019 ◽  
Vol 9 (22) ◽  
pp. 6471-6481 ◽  
Author(s):  
Narasimha Swamy Thirukovela ◽  
Ramesh Balaboina ◽  
Vinayak Botla ◽  
Ravinder Vadde ◽  
Sreekantha Babu Jonnalagadda ◽  
...  
Keyword(s):  
Intramolecular Cyclization ◽  
Pd Nanoparticles ◽  
Environmentally Benign ◽  
Water Medium ◽  
Sonogashira Coupling ◽  
One Pot ◽  
Peg 400 ◽  
Sequential Coupling ◽  
Substituted Pyrazoles

Catalyst efficacy of in situ generated Pd-nanoparticles in the regioselective one-pot synthesis of substituted pyrazoles and isoxazoles via sequential coupling-cyclization methodology in environmentally benign medium is described.

Hexafluorosilicic Acid as a Novel Reagent for the Desilylation of Silylacetylenes: Application in Sequential Sonogashira Coupling and Click Reaction

Synthesis ◽  
2017 ◽  
Vol 49 (11) ◽  
pp. 2374-2388 ◽  
Author(s):  
Ádám Sinai ◽  
Ádám Mészáros ◽  
Ádám Balogh ◽  
Márton Zwillinger ◽  
Zoltán Novák
Keyword(s):  
Aqueous Solution ◽  
Click Reaction ◽  
Aryl Halides ◽  
Environmentally Benign ◽  
Sonogashira Coupling ◽  
One Pot ◽  
Sequential Coupling

Hexafluorosilicic acid was utilized as a novel, cheap, readily available, and environmentally benign alternative reagent for the desilylation of 1-trimethylsilylacetylenes. The applicability of the aqueous solution of the hexafluorosilicic acid was demonstrated in the sequential coupling of aryl halides and ethynyltrimethylsilane to afford internal acetylenes, benzofurans, and triazoles in one-pot Sonogashira–Sonogashira­ and Sonogashira–CuAAC reactions.

Molybdenum-Mediated One-Pot Synthesis of Pyrazoles from Isoxazoles

Synthesis ◽  
2019 ◽  
Vol 51 (20) ◽  
pp. 3796-3804 ◽  
Author(s):  
Marine Rey ◽  
Stéphane Beaumont
Keyword(s):  
Bond Cleavage ◽  
Direct Synthesis ◽  
Molybdenum Complex ◽  
One Pot ◽  
One Pot Synthesis ◽  
Wide Range ◽  
Hydrolysis Of ◽  
Substituted Pyrazoles

A one-pot approach for the direct synthesis of substituted pyrazoles from isoxazoles is reported. The process involves isoxazole N–O bond cleavage mediated by a molybdenum complex, in situ hydrolysis of the resulting β-amino enone to the corresponding 1,3-diketone, followed by pyrazole formation in the presence of hydrazine or substituted hydrazine. Good to excellent yields and regioselectivities are obtained with nonsymmetric isoxazoles. By using readily available starting materials, a wide range of substituted pyrazoles may be synthesized by this method.

Expeditious Scalable Catalyst-Free One-Pot Synthesis of 4-Alkoxy-5-amino-3-methylthiophene-2-carbonitriles via Sequential Reactions­ of Lithiated Alkoxyallenes with Isothiocyanates and 2-Bromoacetonitrile

Synthesis ◽  
2018 ◽  
Vol 50 (09) ◽  
pp. 1891-1900 ◽  
Author(s):  
Nina Nedolya ◽  
Boris Trofimov ◽  
Olga Tarasova ◽  
Alexander Albanov
Keyword(s):  
Intramolecular Cyclization ◽  
Thiophene Ring ◽  
One Pot ◽  
One Pot Synthesis ◽  
Convenient Approach ◽  
Reaction Proceeds ◽  
Sequential Addition ◽  
In Situ Formation ◽  
Cyano Groups

A synthetically simple and convenient approach to tetrasubstituted thiophenes with rare combination of the alkoxy, amino, and cyano groups has been developed. The assembly of polyfunctionalized thiophene ring is implemented in one preparative step by sequential addition of isothiocyanate and 2-bromoacetonitrile to the lithiated (with n-BuLi) alkoxyallene. The reaction proceeds through in situ formation and intramolecular cyclization of cyanomethyl 2-alkoxy-N-buta-2,3-dienimidothioate (1-aza-1,3,4-triene).

scholarly journals One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation

2021 ◽  
Vol 8 ◽  
Author(s):  
Fa-Jie Chen ◽  
Zhenguo Hua ◽  
Jianhui Chen ◽  
Jiajia Chen ◽  
Daesung Lee ◽  
...  
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Copper Catalyst ◽  
High Yield ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Acid Chlorides ◽  
Triflic Acid ◽  
One Pot

Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.

An Efficient Synthesis of Substituted Pyrazoles from One-Pot Reaction of Ketones, Aldehydes, and Hydrazine Monohydrochloride

Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1071-1075 ◽  
Author(s):  
Vit Lellek ◽  
Cheng-yi Chen ◽  
Wanggui Yang ◽  
Jie Liu ◽  
Xuebao Ji ◽  
...  
Keyword(s):  
Efficient Synthesis ◽  
One Pot ◽  
Metal Free ◽  
Mild Conditions ◽  
Free Process ◽  
One Pot Condensation ◽  
Substituted Pyrazoles

An efficient, one-pot and metal-free process for the preparation of 3,5-disubstituted and 3,4,5-trisubstituted pyrazoles on multi-gram scale was developed. One-pot condensation of ketones, aldehydes and hydrazine monohydrochloride readily formed pyrazoline intermediates under mild conditions. Oxidation of pyrazolines, in situ, employing bromine afforded a wide variety of pyrazoles. The methodology offers a fast, and often chromatography-free protocol for the synthesis of 3,4,5-substituted pyrazoles in good to excellent yields. Alternatively, a more benign oxidation protocol affords 3,5-disubstituted or 3,4,5-trisubstituted pyrazoles by simply heating pyrazolines in DMSO under oxygen.

Catalyst-Free Synthesis of 3-(2-Quinolinemethylene)-Substituted Isoindolinones in Water

Synthesis ◽  
2018 ◽  
Vol 50 (11) ◽  
pp. 2255-2265 ◽  
Author(s):  
Feng Xu ◽  
Youping Tian ◽  
Jialin Sun ◽  
Kaihua Zhang ◽  
Gaoqiang Li
Keyword(s):  
Intramolecular Cyclization ◽  
Environmentally Benign ◽  
Primary Amines ◽  
One Pot ◽  
Direct Construction ◽  
Type Reaction ◽  
Catalyst Free

A facile and environmentally benign approach toward the synthesis of novel 3-alkyl-substituted isoindolinones by three-component reactions of 2-formylbenzoic acids, primary amines and 2-methyl­azaarenes in water under catalyst- and additive-free conditions is described. This protocol features the direct construction of multiple C–N and C–C bonds via a tandem Mannich-type reaction and intramolecular cyclization in a one-pot fashion, affording the desired 3-(2-quinolinemethylene)-substituted isoindolinones in high to excellent yields.

Unprecedented synthesis of 1,2,3-triazolo-cinnolinone via Sonogashira coupling and intramolecular cyclization

2018 ◽  
Vol 16 (26) ◽  
pp. 4840-4848 ◽  
Author(s):  
Avnish Kumar ◽  
Dharmendra Kumar Tiwari ◽  
Balasubramanian Sridhar ◽  
Pravin R. Likhar
Keyword(s):  
Intramolecular Cyclization ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
One Pot

An unprecedented copper mediated one-pot sequential synthesis of 1,2,3-triazolo cinnolinone derivatives from 2-halo-phenyl triazoles and terminal alkynes has been reported.

Synthesis of Internal Alkynes through an Effective Tandem ­Elimination–Hydrodebromination–Cross-Coupling of gem-­Dibromoalkenes with Halobenzenes

Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 209-214 ◽  
Author(s):  
Yuan Ji ◽  
Ning Zhong ◽  
Zinan Kang ◽  
Guobing Yan ◽  
Ming Zhao
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Coupling ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
Sonogashira Coupling Reaction ◽  
Palladium Catalyzed ◽  
Internal Alkyne

Carbon–carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C–C cross-coupling reaction of two kinds of organic halide, a gem-dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination–hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.

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