Rh(iii)-catalyzed C–H activation reactions forming 1H-isoindoles containing a quaternary carbon center from aryl ketones or benzylamines

2016 ◽  
Vol 52 (66) ◽  
pp. 10171-10174 ◽  
Author(s):  
Yeonhui Yi ◽  
Hyejeong Lee ◽  
Chul-Ho Jun
Keyword(s):  
Microwave Irradiation ◽  
Ammonium Acetate ◽  
Quaternary Carbon ◽  
One Pot ◽  
Aryl Ketones ◽  
Acrylate Esters

Rh(iii)/Cu(OAc)2 catalyzed, one-pot reactions of aryl ketones, acrylate esters and ammonium acetate or α-substituted benzylamines under microwave irradiation conditions produce 1H-isoindoles bearing a quarternary carbon center.

Reactions of Methyl Ketones and (Hetero)arylcarboxamides with N,N-Dimethylacetamide Dimethyl Acetal. A Simple Metal-Free Synthesis of 2,4,6-Trisubstituted Pyridines

2015 ◽  
Vol 68 (2) ◽  
pp. 184 ◽  
Author(s):  
Benjamin Prek ◽  
Uroš Grošelj ◽  
Marta Kasunič ◽  
Silvo Zupančič ◽  
Jurij Svete ◽  
...  
Keyword(s):  
Microwave Irradiation ◽  
Single Crystal ◽  
Ammonium Acetate ◽  
Dimethyl Acetal ◽  
Methyl Ketones ◽  
Closed Vessel ◽  
Simple Metal ◽  
One Pot ◽  
X Ray ◽  
Metal Free

Two metal-free syntheses of 2,4,6-trisubstituted pyridines 10a–m and 16a–j are described. N,N,6-Trimethyl-4-(substituted)pyridin-2-amines 10 were prepared from aryl or heteroaryl methyl ketones which were transformed with N,N-dimethylacetamide dimethyl acetal (DMADMA) into enaminones 4a–m, followed by treatment with ammonium acetate to give (Z)-3-amino-1-(substituted)but-2-en-1-ones 5a–m. These were treated with DMADMA under microwave irradiation in a closed vessel at 130°C, to give via intermediates 7–9 the final products 10a–m. N2,N2,N4,N4-Tetramethyl-6-(substituted) pyridine-2,4-diamines 16a–j were prepared in a one-pot synthesis from the corresponding carboxamides 11a–j by treatment with an excess of DMADMA in a closed vessel under microwave irradiation to give via intermediates 12a–j to 15a–j the final products 16a–j. X-Ray single crystal diffractometry studies of the enaminones 5c, 5g, 5i, 5j, and 5m and 2,4,6-trisubstituted pyridines 16a, 16b, 16g, 16i, and 16j were consistent with the expected structures.

scholarly journals Greener and efficient one-pot synthesis of novel multi-substituted 3-(4,5-diphenyl-1H-imidazol-2-yl)-1H-indole derivatives by using recyclable catalyst under microwave irradiation

2021 ◽  
pp. 261-270 ◽  
Author(s):  
Narendra Nirwan ◽  
Chandresh Pareek
Keyword(s):  
Cost Effectiveness ◽  
Microwave Irradiation ◽  
Ammonium Acetate ◽  
Mass Spectrometric ◽  
Recyclable Catalyst ◽  
The Novel ◽  
Indole Derivatives ◽  
Time Cost ◽  
One Pot ◽  
Short Reaction Time

The novel class of multi-substituted indolylimidazole derivatives series substituted 3-(4,5-diphenyl-1H-imidazol-2-yl)-1H-indole and substituted 5-bromo-3-(4,5-diphenyl-1H-imidazol-2-yl)-1H-indole was synthesized utilising a green and efficient one-pot four components condensation of indole-3-carbaldehyde, benzil, ammonium acetate and various amines under microwave irradiation using Amberlyst A-15 as a recyclable catalyst. The catalyst Amberlyst A-15 has recovered from the reaction mixture and reused repeatedly for the next reaction. The key advantage of this process involves eco-friendly, very short reaction time, cost-effectiveness with the reusability of catalyst, easy workup, and purification of the product with excellent yields. FTIR, 1HNMR and Mass spectrometric studies analyzed and established the structures of all newly synthesized compounds.

A Facile Procedure for Synthesis of Several 1, 4, 5-Trisubstituted-1Himidazole- 2(3H)-ones and -thiones via a One-pot Three-portion Reaction in Solvent and Microwave Irradiation

2019 ◽  
Vol 16 (2) ◽  
pp. 104-109
Author(s):  
Mohammad Shaker
Keyword(s):  
Acetic Acid ◽  
Microwave Irradiation ◽  
Glacial Acetic Acid ◽  
Ammonium Acetate ◽  
Fluorescence Properties ◽  
Irradiation Condition ◽  
One Pot ◽  
Three Component Reaction

An ordinary procedure for the synthesis of several 1, 4, 5-trisubstituted-1H-imidazole- 2(3H)-ones and -thiones by a one-pot three-component reaction of glacial acetic acid under solvent, microwave irradiation condition is proposed. The products were formed through cyclization of benzoin with isothiocyanates or isocyanates and ammonium acetate. All incorporated combinations were determined for their spectral and microanalytical information. These compounds were subsequently studied for their fluorescence properties.

scholarly journals ONE-POT SYNTHESIS OF <em>N</em>-ALKYLATED 2-PYRIDONE DERIVATIVES UNDER MICROWAVE IRRADIATION

2020 ◽  
Author(s):  
Ikram BABA AHMED ◽  
Zahira KIBOU ◽  
Pilar VÁZQUEZ-TATO ◽  
Julio SEIJAS ◽  
Noureddine CHOUKCHOU-BRAHAM
Keyword(s):  
Microwave Irradiation ◽  
One Pot ◽  
One Pot Synthesis

scholarly journals Tandem Fries Reaction–Conjugate Addition under Microwave Irradiation in Dry Media; One-pot Synthesis of Flavanones

1999 ◽  
Vol 23 (9) ◽  
pp. 574-575
Author(s):  
Firouz Matloubi Moghaddam ◽  
Mohammad Ghaffarzadeh ◽  
Seyed Hossein Abdi-Oskoui
Keyword(s):  
Microwave Irradiation ◽  
Silica Gel ◽  
Conjugate Addition ◽  
Solvent Free ◽  
Naphthalene Derivatives ◽  
One Pot ◽  
Fries Rearrangement ◽  
One Pot Synthesis ◽  
Solvent Free Conditions ◽  
Fries Reaction

An AICl3–ZnCl2 mixture supported on silica gel is found to be an efficient medium for the Fries rearrangement of acyloxybenzene or naphthalene derivatives in solvent-free conditions under microwave irradiation.

scholarly journals A new one-pot three-component synthesis of 4-aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation

Synthesis ◽  
2021 ◽  
Author(s):  
Muhammad Syafiq Bin Shahari ◽  
Ahmad Junaid ◽  
Edward R. T. Tiekink ◽  
Anton V. Dolzhenko
Keyword(s):  
Microwave Irradiation ◽  
Aromatic Aldehydes ◽  
Antileukemic Activity ◽  
One Pot ◽  
Biological Screening ◽  
X Ray ◽  
X Ray Crystallography ◽  
Cyclic Amines ◽  
Three Component Reaction ◽  
Fast Synthesis

A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed. The synthesis is performed under microwave irradiation in a one-pot manner from cyanoguanidine, aromatic aldehydes, and cyclic amines. Their three-component reaction in the presence of hydrochloric acid produced dihydrotriazines, which were then converted (without isolation) to the targeted compounds via aromatic dehydrogenation in the presence of alkali. The reaction tolerated various aromatic aldehydes (including heterocyclic) and cyclic amines. Crystal structures of two representative 4-aryl-6-morpholino-1,3,5-triazin-2-amines were established by X-ray crystallography. The results of preliminary biological screening identified potent antileukemic activity for 6-(3,4-dihydroisoquinolin-2(1<i>H</i>)-yl)-4-phenyl-1,3,5-triazin-2-amine.

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