Urea–Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel

Synlett ◽  
2018 ◽  
Vol 30 (02) ◽  
pp. 225-229 ◽  
Author(s):  
Cristian Ochoa-Puentes ◽  
Natalia Higuera ◽  
Diana Peña-Solórzano
Keyword(s):  
Catalytic Activity ◽  
Aromatic Aldehyde ◽  
Zinc Chloride ◽  
Ammonium Acetate ◽  
Reaction Medium ◽  
Eutectic Mixture ◽  
One Pot ◽  
Dicarbonyl Compound ◽  
Excellent Yield ◽  
One Pot Synthesis

The low-melting mixture urea–ZnCl2 was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1H-imidazoles or 2-aryl-1H-phenanthro[9,10-d]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.

Tributylhexadecylphosphonium bromide: an efficient reagent system for the one-pot synthesis of 2,4,5-trisubstituted imidazoles

2015 ◽  
Vol 21 (2) ◽  
Author(s):  
Mohammad Heidari ◽  
Mohsen Rezaei ◽  
Rashid Badri
Keyword(s):  
Cost Effectiveness ◽  
Aromatic Aldehyde ◽  
Ammonium Acetate ◽  
Reaction Times ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
The One ◽  
Efficient Reagent

AbstractThe reaction of benzil, an aromatic aldehyde, and ammonium acetate in ethanol at reflux in the presence of tributylhexadecylphosphonium bromide as catalyst affords a 2,4,5-trisubstituted imidazole. The present methodology offers several advantages over the literature methods, including excellent yields, shorter reaction times, environmentally benign milder reaction conditions, cost-effectiveness of catalyst, easy workup, and purification of products by nonchromatographic methods.

3,5-Bis(trifluoromethyl) Phenylammonium triflate(BFPAT) as a Novel Organocatalyst for the Efficient Synthesis of 2,3-dihydroquinazolin-4(1H)-one Derivatives

2020 ◽  
Vol 17 (1) ◽  
pp. 40-45
Author(s):  
Mandana Alipour ◽  
Zinatossadat Hossaini ◽  
Samad Khaksar ◽  
Faramarz Rostami-Charati
Keyword(s):  
Ammonium Acetate ◽  
Isatoic Anhydride ◽  
Efficient Synthesis ◽  
Melting Points ◽  
One Pot ◽  
Excellent Yield ◽  
One Pot Synthesis ◽  
New Process

Aim and Objective: A one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives by threecomponent cyclo-condensation of isatoic anhydride, aldehydes and amine or ammonium acetate has been developed using 3,5-Bis(trifluoromethyl) phenylammonium triflate (BFPAT) as a new organocatalyst. Material and method: All of the obtained products are known compounds and identified by IR, 1HNMR, 13CNMR and melting points. Results: A wide variety of structurally different aldehydes reacted easily and rapidly to result in the relating 2,3-dihydroquinazolin-4(1H)-ones in good to excellent yield. Conclusion: We have demonstrated an extremely effective and new process for synthesizing 2,3- dihydroquinazolin-4(1H)-ones employing BFPAT as a novel organocatalyst in one-pot fashion.

An Expeditious One-Pot Three-Component Synthesis of 4-Aryl-3,4-dihydrobenzo[g] quinoline-2,5,10(1H)-triones under Green Conditions

2020 ◽  
Vol 23 (23) ◽  
pp. 2626-2634
Author(s):  
Saiedeh Kamalifar ◽  
Hamzeh Kiyani
Keyword(s):  
Reaction Medium ◽  
Meldrum's Acid ◽  
Meldrum’S Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
Substituted Benzaldehydes ◽  
High Yields ◽  
First Time ◽  
Green Conditions

: An efficient and facial one-pot synthesis of 4-aryl-3,4-dihydrobenzo[g]quinoline- 2,5,10(1H)-triones was developed for the first time. The process proceeded via the three-component cyclocondensation of 2-amino-1,4-naphthoquinone with Meldrum’s acid and substituted benzaldehydes under green conditions. The fused 3,4-dihydropyridin-2(1H)- one-ring naphthoquinones have been synthesized with good to high yields in refluxing ethanol as a green reaction medium. This protocol is simple and effective as well as does not involve the assistance of the catalyst, additive, or hazardous solvents.

ChemInform Abstract: Polyethylene Glycol (PEG-400): A Mild and Efficient Reaction Medium for One-Pot Synthesis of 3-Hydroxy-3-(pyridin-2-ylmethyl)indolin-2-ones.

ChemInform ◽  
2013 ◽  
Vol 44 (42) ◽  
pp. no-no
Author(s):  
M. Raghu ◽  
M. Rajasekhar ◽  
B. Chandra Obula Reddy ◽  
C. Suresh Reddy ◽  
B. V. Subba Reddy
Keyword(s):  
Polyethylene Glycol ◽  
Reaction Medium ◽  
One Pot ◽  
Peg 400 ◽  
One Pot Synthesis

Solvent-free, one-pot synthesis of 2,4,6-triarylpyridines using trichloroisocyanuric acid or N-bromosuccinimide as a novel and neutral catalyst

2011 ◽  
Vol 76 (11) ◽  
pp. 1307-1315 ◽  
Author(s):  
Behrooz Maleki ◽  
Hafezeh Salehabadi ◽  
Zeinalabedin Sepehr ◽  
Mina Kermanian
Keyword(s):  
Ammonium Acetate ◽  
Solvent Free ◽  
One Pot ◽  
Aryl Aldehydes ◽  
One Pot Synthesis ◽  
Solvent Free Conditions ◽  
Trichloroisocyanuric Acid

A simple and benign protocol has been explored for the preparation of 2,4,6-triarylpyridines by a one-pot reaction between aryl aldehydes, enolizable ketones and ammonium acetate in the presence of N-bromosuccinimide or trichloroisocyanuric acid as green and neutral catalysts. The reactions proceed smoothly at 130 °C under solvent-free conditions to provide 2,4,6-triarylpyridines in good yields.

Polyethylene glycol (PEG-400): a mild and efficient reaction medium for one-pot synthesis of 3-hydroxy-3-(pyridin-2-ylmethyl)indolin-2-ones

2013 ◽  
Vol 54 (27) ◽  
pp. 3503-3506 ◽  
Author(s):  
M. Raghu ◽  
M. Rajasekhar ◽  
B. Chandra Obula Reddy ◽  
C. Suresh Reddy ◽  
B.V. Subba Reddy
Keyword(s):  
Polyethylene Glycol ◽  
Reaction Medium ◽  
One Pot ◽  
Peg 400 ◽  
One Pot Synthesis
Sign in / Sign up

Export Citation Format

Share Document