Cerium (IV) Ammonium Nitrate (CAN) Mediated Reactions IV. A Highly Efficient Synthesis of N,N’-Diarylsubstituted Formamidines in Water at Ambient Temperature

Sadek, Kamal Usef; Alnajjar, Abdulaziz; Mekheimer, Ramadan Ahmed; Mohamed, Nasr Kamel; Mohamed, Haney A.

doi:10.4236/gsc.2011.13015

Cited by 15 publications

(8 citation statements)

References 38 publications

(36 reference statements)

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“…Some of the formamidine synthesis has also been performed in organic solvent like acetic acid under thermal conditions, reduction of 1,3‐disubstituted urea in pyridine and catalytic hydrogenation of carbodiimides . The other methods involving synthesis of formamidines are reduction of carbamide by sodium borohydride in isopropanol, use of catalyst like sulfated zirconia, hexafluroisoproanol as fluorinated solvent, cerium (IV) ammonium nitrate . However, some of these protocols are generally associated with one or more disadvantages, such as long reaction times, high reaction temperatures, low yields, complex handling procedures, problematic side reactions, environmental concerns associated with the use of metal and acidic catalysts, use of organic solvents, etc.…”

Section: β‐Cyclodextrin Catalyzed Organic Transformationsmentioning

confidence: 99%

β‐Cyclodextrin: A Green and Efficient Supramolecular Catalyst for Organic Transformations

Dalal

Patil

Tayade

2018

The Chemical Record

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β-Cyclodextrin is cyclic oligosaccharide possessing hydrophobic cavity, which binds the substrates selectively and catalyze number of organic transformations with high selectivity. It catalyzes the reaction by non-covalent supramolecular bonding with reversible formation of host-guest complexes as seen in enzymes. This account summarizes our efforts in designing a good number of important organic transformations using β-cyclodextrin and its derivatives. These reactions were performed in neat, aqueous as well as organic media. Greener synthetic routes to a variety of biologically relevant organic molecules has been developed. The temperature, solvent and catalyst amount plays in important role in these reactions. β-Cyclodextrin activates variety of organic compounds like aldehydes, ketones, anhydride, oximes, amines, nitriles and increases the rate of reactions.

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Section: β‐Cyclodextrin Catalyzed Organic Transformationsmentioning

confidence: 99%

β‐Cyclodextrin: A Green and Efficient Supramolecular Catalyst for Organic Transformations

Dalal

Patil

Tayade

2018

The Chemical Record

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“…Exchange reactions of N,N -dimethylformamidines or acetamidines by a variety of amines have been reported to be the most popular method for the synthesis of symmetrical and unsymmetrical formamidines. We have developed a simple and green route for the synthesis of N,N?-diaryl-formamidines 124 via the reaction of aromatic amines with triethylorthoformate 123 in water at room temperature catalyzed by CAN acting as a Lewis acid catalyst (Scheme 29 and Table 21) [87]. Green Chemistry Letters and Reviews 207…”

Section: Solvent-free Reactionsmentioning

confidence: 99%

Green methodologies in organic synthesis: recent developments in our laboratories

Hafez

Al‐Mousawi

Moustafa

et al. 2013

Green Chemistry Letters and Reviews

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The results of the studies carried out in our laboratories during the last 15 years, aimed at developing green methodologies for the synthesis of polyfunctionalized heteroaromatic substances, are surveyed. The results of the investigations demonstrate that green methodologies are not only less hazard than classical preparative methods but they also are more efficient and economical. For example, short reaction times and higher yields are observed for reactions in which conventional heating is replaced by microwave or ultrasound irradiation. The implementation of multicomponent reactions in green preparative routes also reduces the cost of carrying out the reactions because multiple separation and crystallization steps are avoided. In general, by employing the new green methodologies we have been able to produce a large number of polyfunctional aromatic substances in a highly efficient manner.

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“…In recent decades, N, N'-diaryl formamidines and their anions have been widely used in various fields of organic and medicinal chemistry. [18][19][20][21] These types of compounds have many biological and pharmaceutical properties, including antimalarial, [22] anesthetic, [23] ultraviolet light absorbent, [24] antihypertensive, [25] and renal dipeptidase inhibitory [26] activities.…”

Section: Introductionmentioning

confidence: 99%

Introduction of Two New Brønsted Acidic Ionic Liquids for the Formamide and Formamidine Derivatization of Amines

et al. 2020

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In this study, two recently reported 1,4-diazabicyclo[2.2.2] octane (DABCO)-based ionic liquids were used for the acceleration of the N-formylation of primary and secondary amines with formic acid under solvent-free conditions. These reagents have also been used for the efficient synthesis of N, N'-diaryl formamidines through reaction of triethyl orthoformate with primary aryl amines. These methods offer several advantages such as excellent yields, short reaction times and simple workup with the environmentally friendly procedure.

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Cerium (IV) Ammonium Nitrate (CAN) Mediated Reactions IV. A Highly Efficient Synthesis of N,N’-Diarylsubstituted Formamidines in Water at Ambient Temperature

Cited by 15 publications

References 38 publications

β‐Cyclodextrin: A Green and Efficient Supramolecular Catalyst for Organic Transformations

β‐Cyclodextrin: A Green and Efficient Supramolecular Catalyst for Organic Transformations

Green methodologies in organic synthesis: recent developments in our laboratories

Introduction of Two New Brønsted Acidic Ionic Liquids for the Formamide and Formamidine Derivatization of Amines

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