Convenient One-Pot Synthesis of 9H-Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst

Synthesis ◽  
2021 ◽  
Author(s):  
Darío C. Gerbino ◽  
H. Sebastián Steingruber ◽  
Pamela Mendioroz ◽  
María A. Volpe
Keyword(s):  
Microwave Irradiation ◽  
Direct Synthesis ◽  
Reaction Times ◽  
One Pot ◽  
One Pot Synthesis ◽  
Ligand Free ◽  
Palladium Catalyzed ◽  
Scalable Synthesis ◽  
The One ◽  
High Yields

AbstractAn efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9H-carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald–Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9H-carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.

One-pot Synthesis of Dibenzofurans via SNAr and Subsequent Ligand-free Palladium-catalyzed Intramolecular Aryl-aryl Cross-coupling Reactions under Microwave Irradiation

2011 ◽  
Vol 66 (8) ◽  
pp. 833-836
Author(s):  
Zhiping Che ◽  
Hui Xu
Keyword(s):  
Microwave Irradiation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Cross Coupling Reactions ◽  
Ligand Free ◽  
Palladium Catalyzed ◽  
Snar Reaction

An efficient one-pot synthesis of dibenzofurans, via SNAr reaction of aryl halides and ortho-bromophenols in the presence of anhydrous K2CO3 and subsequent ligand-free palladium-catalyzed intramolecular aryl-aryl cross-coupling cyclization under microwave irradiation, is described.

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.

Rapid and Green One-Pot Synthesis of Novel 2-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-diones

2021 ◽  
Vol 18 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Zahra Ghahremany ◽  
Madieh Sadeghpour
Keyword(s):  
Aromatic Amines ◽  
Low Cost ◽  
Guanidine Hydrochloride ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
The One ◽  
High Yields ◽  
Work Up

: A green and efficient protocol was developed for the one-pot three-component synthesis of novel 2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-(arylamino)-1H-indene-1,3(2H)-dione derivatives by the reaction of 4-hydroxycoumarin, ninhydrin and aromatic amines in the presence of guanidine hydrochloride as an organocatalyst under solvent-free conditions. The present approach offers several advantages such as low cost, simple work-up, short reaction times, chromatography-free purification, high yields and greener conditions.

scholarly journals Calcium hydroxide: An efficient and mild base for one-pot synthesis of curcumin and it’s analogues

2013 ◽  
Vol 6 (1) ◽  
pp. 150-156
Author(s):  
Pramod S. Kulkarni ◽  
Dasharath D. Kondhare ◽  
Ravi Varala ◽  
Pudukulathan K. Zubaidha
Keyword(s):  
Calcium Hydroxide ◽  
Aromatic Aldehyde ◽  
One Pot ◽  
Acetyl Acetone ◽  
One Pot Synthesis ◽  
The One ◽  
High Yields

Abstract Calcium hydroxide was found to be an efficient mild base for the one-pot synthesis of curcumin and its analogues obtained by condensation of one equivalent of acetyl acetone with two equivalents of corresponding aromatic aldehyde. The present protocol offers various advantages such as high yields, inexpensive easily available mild base, easy workup and eco-friendly method.

A One-Pot, Three-Component, Solvent-Free Synthesis of Novel 6H-Chromeno[3’,4’:5,6]Pyrido[2,3-d]Pyrimidine-Triones under Microwave Irradiation

2018 ◽  
Vol 42 (12) ◽  
pp. 604-607
Author(s):  
Loghman Firoozpour ◽  
Hoda Yahyavi ◽  
Ramona Ejtemaei ◽  
Setareh Moghimi ◽  
Alireza Foroumadi
Keyword(s):  
Microwave Irradiation ◽  
Efficient Method ◽  
Barbituric Acid ◽  
Reaction Times ◽  
Solvent Free ◽  
One Pot ◽  
Solvent Free Conditions ◽  
Substituted Benzaldehydes ◽  
High Yields ◽  
Solvent Free Synthesis

A green and efficient method for preparing novel heterocyclic systems is established through the reaction of differently substituted benzaldehydes, barbituric acid and 4-amino-2H-chromene-2-one under solvent-free conditions. This method affords 6H-chromeno[3’,4’:5,6] pyrido[2,3-d]pyrimidine-trione derivatives in high yields and short reaction times.

scholarly journals Efficient Cu-catalyzed base-free C–S coupling under conventional and microwave heating. A simple access to S-heterocycles and sulfides

2013 ◽  
Vol 9 ◽  
pp. 467-475 ◽  
Author(s):  
Silvia M Soria-Castro ◽  
Alicia B Peñéñory
Keyword(s):  
Microwave Irradiation ◽  
Microwave Heating ◽  
Catalytic System ◽  
Low Cost ◽  
One Pot ◽  
Alkyl Aryl ◽  
One Pot Synthesis ◽  
Aryl Iodides ◽  
The One ◽  
Aryl Sulfides

S-aryl thioacetates can be prepared by reaction of inexpensive potassium thioacetate with both electron-rich and electron-poor aryl iodides under a base-free copper/ligand catalytic system. CuI as copper source affords S-aryl thioacetates in good to excellent yields, by using 1,10-phenanthroline as a ligand in toluene at 100 °C after 24 h. Under microwave irradiation the time was drastically reduced to 2 h. Both procedures are simple and involve a low-cost catalytic system. This methodology was also applied to the “one-pot” synthesis of target heterocycles, such as 3H-benzo[c][1,2]dithiol-3-one and 2-methylbenzothiazole, alkyl aryl sulfides, diaryl disulfides and asymmetric diaryl sulfides in good yields.

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