scholarly journals A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

2017 ◽  
Vol 13 ◽  
pp. 1900-1906 ◽  
Author(s):  
Grzegorz Mlostoń ◽  
Paulina Pipiak ◽  
Róża Hamera-Fałdyga ◽  
Heinz Heimgartner
Keyword(s):  
Equimolar Amount ◽  
One Pot ◽  
Efficient Approach ◽  
Highly Efficient ◽  
High Yields

Trimethylsilyldiazomethane (TMS-CHN2) reacts readily with hetaryl thioketones to give sterically crowded 2-trimethylsilyl-4,4,5,5-tetrahetaryl-1,3-dithiolanes with complete regioselectivity at −75 °C as well as at rt. Thiofluorenone, a relatively stable and highly reactive aryl thioketone, yields upon treatment with TMS-CHN2 at −60 °C the corresponding 1,3,4-thiadiazoline. This unstable cycloadduct undergoes decomposition at ca. −45 °C and the silylated thiocarbonyl S-methanide generated thereby is trapped with complete regioselectivity by aryl or hetaryl thioketones forming also sterically crowded 2-trimethylsilyl-1,3-dithiolanes. The obtained 1,3-dithiolanes, by treatment with an equimolar amount of TBAF in a one-pot procedure, are converted in high yields into hetaryl/aryl-substituted ethenes or dibenzofulvenes, respectively, via a cycloreversion reaction of the intermediate 1,3-dithiolane carbanion. The presented protocol offers a new, highly efficient approach to tetrasubstituted ethenes and dibenzofulvenes bearing aryl and/or hetaryl substituents.

A highly efficient and green approach for the synthesis of pyrimido[4,5-b]quinolines using N,N-diethyl-N-sulfoethanaminium chloride

2021 ◽  
Vol 76 (2) ◽  
pp. 85-90
Author(s):  
Abdolkarim Zare ◽  
Manije Dianat
Keyword(s):  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Catalyst Amount ◽  
Green Protocol ◽  
Highly Efficient ◽  
Green Approach ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields

Abstract A highly efficient and green protocol for the synthesis of pyrimido[4,5-b]quinolines has been described. The one-pot multicomponent reaction of dimedone with arylaldehydes and 6-amino-1,3-dimethyluracil in the presence of N,N-diethyl-N-sulfoethanaminium chloride ([Et3N–SO3H][Cl]) as an ionic liquid (IL) catalyst under solvent-free conditions afforded the mentioned compounds in high yields and short reaction times. Our protocol is superior to many of the reported protocols in terms of two or more of these factors: the reaction times, yields, conditions (solvent-free versus usage of organic solvents), temperature and catalyst amount.

A highly efficient asymmetric synthesis of quaternary stereocenter-containing indolizidine and quinolizidine alkaloids using aldehydes, nitroalkenes, and unactivated cyclic ketimines

2014 ◽  
Vol 50 (100) ◽  
pp. 15913-15915 ◽  
Author(s):  
Yu Tan ◽  
Yong-Jian Chen ◽  
Hua Lin ◽  
Han-Lin Luan ◽  
Xing-Wen Sun ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Quinolizidine Alkaloids ◽  
One Pot ◽  
Efficient Approach ◽  
Highly Efficient ◽  
Quaternary Stereocenter

A highly efficient approach to the construction of indolizidines and quinolizidines bearing a bridged quaternary stereocenter has been established in a one-pot fashion using aldehydes, nitroalkenes, and cyclic ketimines.

Efficient one-pot fructose to DFF conversion using sulfonated magnetically separable MOF-derived Fe3O4 (111) catalysts

2017 ◽  
Vol 19 (3) ◽  
pp. 647-655 ◽  
Author(s):  
Ruiqi Fang ◽  
Rafael Luque ◽  
Yingwei Li
Keyword(s):  
Heterogeneous Catalyst ◽  
One Pot ◽  
Highly Efficient ◽  
Magnetically Separable ◽  
High Yields

A highly efficient and recyclable non-noble heterogeneous catalyst is developed for one-pot conversion of fructose into 2,5-diformylfuran with extremely high yields (>99%).

Synthesis of a series of novel 2,3-dihydrofuranonaphthoquinone derivatives

2017 ◽  
Vol 41 (8) ◽  
pp. 448-451 ◽  
Author(s):  
Maryam Salari ◽  
Mohammad H. Mosslemin ◽  
Alireza Hassanabadi
Keyword(s):  
Reaction Time ◽  
Green Chemistry ◽  
Organic Solvent ◽  
Aromatic Aldehyde ◽  
Efficient Synthesis ◽  
One Pot ◽  
Short Reaction Time ◽  
Highly Efficient ◽  
One Pot Condensation ◽  
High Yields

A green and highly efficient synthesis of 12 novel trans-2-(4-chlorobenzoyl)-3-aryl-2,3-dihydronaphtho[2,3- b]furan-4,9-diones has been achieved via a three-component, one-pot condensation of 2-[2-(4-chlorophenyl)-2-oxoethyl)]isoquinolinium bromide with 2-hydroxy-1,4-naphthoquinone and an aromatic aldehyde in the presence of catalytic amounts of choline hydroxide in water under reflux conditions. The advantages of this method are a short reaction time, high yields and the avoidance of any hazardous organic solvent. Therefore, this procedure can be classified as green chemistry.

scholarly journals DOWEX(R)50WX4/H2O: A Green System for a One-pot and Three-Component Synthesis of isoxazol-5(4H)-one Derivatives

2017 ◽  
Vol 59 (3) ◽  
Author(s):  
Davood Setamdideh
Keyword(s):  
Present Method ◽  
Reaction Times ◽  
One Pot ◽  
Efficient Approach ◽  
High Yields ◽  
Green System ◽  
Reaction Profile ◽  
Operational Simplicity

A one-pot and three-component synthesis of 3-methyl-4-arylmethyleneisoxazol-5(4<em>H</em>)-ones was developed in the presence of DOWEX(R)50WX4 as the catalyst. The products were obtained in high yields (93-96%) and short reaction times (30-60 min). The present method provides an easy and efficient approach for the synthesis of this class of compounds, because of its clean reaction profile and operational simplicity.

scholarly journals Microwave-Assisted Three-Component “Catalyst and Solvent-Free” Green Protocol: A Highly Efficient and Clean One-Pot Synthesis of Tetrahydrobenzo[b]pyrans

2014 ◽  
Vol 2014 ◽  
pp. 1-8 ◽  
Author(s):  
Sougata Santra ◽  
Matiur Rahman ◽  
Anupam Roy ◽  
Adinath Majee ◽  
Alakananda Hajra
Keyword(s):  
Knoevenagel Condensation ◽  
One Pot ◽  
Green Protocol ◽  
Microwave Assisted ◽  
Highly Efficient ◽  
One Pot Synthesis ◽  
Purification Technique ◽  
The One ◽  
High Yields ◽  
Operational Simplicity

A green and highly efficient method has been developed for the one-pot synthesis of tetrahydrobenzo[b]pyrans via a three-component condensation of aldehydes, 1,3-cyclic diketones, and malononitrile under MW irradiation without using any catalyst and solvent. This transformation presumably occurs by a sequential Knoevenagel condensation, Michael addition, and intramolecular cyclization. Operational simplicity, solvent and catalyst-free conditions, the compatibility with various functional groups, nonchromatographic purification technique, and high yields are the notable advantages of this procedure.

scholarly journals A Highly Efficient Approach to the Synthesis of Complex α-Glycosyl Phosphosaccharides

2021 ◽  
Author(s):  
Yugen Zhu ◽  
Xiaojuan Zhang ◽  
Yutong Yang ◽  
Jiahao Ding ◽  
Yun Zhao ◽  
...  
Keyword(s):  
Phosphoric Acid ◽  
Leishmania Donovani ◽  
One Pot ◽  
Efficient Approach ◽  
Highly Efficient ◽  
One Pot Synthesis ◽  
The One

Abstract A highly efficient and stereoselective approach to the synthesis of biologically important and complex α-glycosyl phosphosaccharides (GPSs) has been disclosed, employing direct gold(I)-catalyzed glycosylation of the weakly nucleophilic phosphoric acid acceptors. The broad substrate scope is demonstrated with more than 45 examples, including glucose (Glc), xylose, glucouronatose, galactose (Gal), mannose (Man), rhamnose (Rha), fucose (Fuc), 2-N3-2-dexoxymannose (ManN3), 2-N3-2-dexoxyglucose (GlcN3), 2-N3-2-dexoxygalactose (GalN3) and unnatural carbohydrates. Moreover, the glycosyl phosphotriester prepared herein was successfully applied to the one-pot synthesis of a GPS from Leishmania donovani, and an effective preparation of a trisaccharide diphosphate of GPS fragments from Hansenula capsulate via iterative elongation strategy is realized.

Highly efficient one-pot assembly of peptides by double chemoselective coupling

2017 ◽  
Vol 15 (36) ◽  
pp. 7533-7542 ◽  
Author(s):  
Ivo E. Sampaio-Dias ◽  
Carlos A. D. Sousa ◽  
Sara C. Silva-Reis ◽  
Sara Ribeiro ◽  
Xerardo García-Mera ◽  
...  
Keyword(s):  
One Pot ◽  
Highly Efficient ◽  
High Yields

An efficient and faster methodology for the assembly of oligopeptides by a three-step one-pot protocol with high yields and virtually no epimerization.

Microwave-Assisted and L-proline Catalysed Domino Cyclisation in an Aqueous Medium: A Rapid, Highly Efficient and Green Synthesis of Benzo[a]Phenazine Annulated Heterocycles

2016 ◽  
Vol 40 (12) ◽  
pp. 722-726 ◽  
Author(s):  
Afshin Yazdani-Elah-Abadi ◽  
Razieh Mohebat ◽  
Mehrnoosh Kangani
Keyword(s):  
Green Synthesis ◽  
Reaction Times ◽  
Aromatic Aldehydes ◽  
Heterocyclic Ring ◽  
One Pot ◽  
Microwave Assisted ◽  
Highly Efficient ◽  
High Yields ◽  
Work Up ◽  
Operational Simplicity

A highly efficient one-pot, two-step microwave-assisted procedure was applied for the rapid and green synthesis of benzo[a]phenazine annulated heterocyclic ring systems from the three- or four-component condensation reactions of 2-hydroxynaphthalene-1,4-dione, o-phenylenediamine, aromatic aldehydes and 1,3-indandione using L-proline as a bifunctional organocatalyst in water. This new procedure has a number of advantages such as high yields, very short reaction times, operational simplicity, simple work-up procedures and avoidance of hazardous or toxic catalysts and organic solvents. Moreover, the catalyst can be recovered and reused several times without much loss of its performance.

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