Oxidation of aromatic aldehydes with potassium bromate–bromide reagent and an acidic catalyst

Sharma, Geetika; Robert, Alice R.

doi:10.1007/s11164-012-0836-y

Cited by 14 publications

(10 citation statements)

References 13 publications

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“…Interestingly, functionalized pyrimidouracils can be synthesized via the direct condensation of aromatic aldehydes and N ‐uracil amidines. [ 24 ] However, the use of aldehydes as the coupling partners poses several shortcomings like (a) some active aldehyde groups may undergo an oxidation reaction which can potentially form unwanted by‐products, and therefore, for resisting this, inert conditions are required [ 25 ] ; (b) some reactive aldehydes may undergo a decarbonylation reaction under tough reaction conditions [ 26 ] ; (c) moreover, high cost or nonavailability of some aldehydes such as heteroaryl ones restricted the synthesis of variable products. In order to alleviate these shortcomings, it is necessary to develop more viable and sustainable chemical procedures for the synthesis of this class of molecules.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of functionalized pyrimidouracils by ruthenium‐catalyzed oxidative insertion of (hetero)aryl methanols into N‐uracil amidines

Debnath

Sahu²,

2020

Applied Organom Chemis

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A dehydrogenative coupling of N‐uracil amidines with (hetero)aryl methanols has been developed, allowing for the facile synthesis of a broad range of structurally diverse pyrimidouracils. By applying [RuCl2(p‐cymene)]2/Cs2CO3 as an efficient catalytic system, the easily available, cheap (hetero)aryl methanols were firstly employed for oxidative insertion/CH amination into the N‐uracil amidines, providing highly functionalized pyrimido[4,5‐d]pyrimidine‐2,4‐diones. Due to the better stability of alcohols than aldehydes, this synthetic protocol is applicable to a broad range of alcoholic substrates and does not required any protection during the whole preparation process. The presented protocol has the potential to prepare valuable products which cannot be accessed presently or extremely arduous to procure by following regular procedure. Hence, this is a remarkably improved protocol compared with the existing methodologies. The overall reaction sequence is an effective oxidation‐imination‐cyclization tandem process catalyzed by ruthenium catalyst.

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Section: Introductionmentioning

confidence: 99%

Synthesis of functionalized pyrimidouracils by ruthenium‐catalyzed oxidative insertion of (hetero)aryl methanols into N‐uracil amidines

Debnath

Sahu²,

2020

Applied Organom Chemis

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“…This one-step synthesis of N-substituted amidines from nitriles and amines can be realized only if the nitriles are activated either by electron-withdrawing groups [22] with benzaldehydes under transition metal free conditions [32]. However, the use of aldehydes as the coupling partners poses several shortcomings like-(i) some active aldehyde groups may undergo an oxidation reaction which can potentially form unwanted by-products, and therefore, for resisting this, inert conditions are required [33]; (ii) some reactive aldehydes may undergo a decarbonylation reaction under tough reaction conditions [34]; (iii) moreover, high cost or non-availability of some aldehydes such as-heteroaryl ones, restricted the synthesis of variable products. In order to alleviate these shortcomings, we have developed another synthetic protocol for the preparation of 1,3,5,7tetrasubstituted pyrimido[4,5-d]pyrimidines via TBHP-mediated direct oxidative coupling of N-uracil amidines and under metal-free conditions [35].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Amidines and Its Application to Pyrimidouracil Synthesis

Debnath

2020

The 24th International Electronic Conference on Synthetic Organic Chemistry

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Amidines are the important classes of nitrogenous compounds, which have been widely used as antibiotics, diuretics, antiphogistic drugs, anthelmintics, and acaricides. They represent an important pharmacophore in modern drug discovery, and can be found in DNA and RNA binding diamidine diminazene, ASIC inhibitor, muscarinic agonists for the treatment of Alzheimer's disease, platelet aggregation inhibitors, and recently, serine protease inhibitors, to give some examples. These enormous significant applications have attracted the research community towards the development of simple and economically viable methods for the synthesis of amidines. In this paper, we have demonstrated a synthetic protocol for the preparation of amidines via copper catalyzed nucleophilic addition of amines into nitriles. The reaction proceeds smoothly at 100 °C in the presence of CuCl, Cs2CO3 and 2,2 /bipyridine as ligand in TFE solvent. Moreover, an efficient protocol for the synthesis of substituted pyrimidouracils via PhI(OAc)2-mediated oxidative coupling of N-uracil amidines and methylarenes under metal-free conditions has been developed. The starting materials N-uracil amidines were synthesized from 6-chlorouracil and amidines via nucleophilic substitution reactions.

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“…(1) the active aldehyde groups may easily suffer from an oxidation reaction, leading to formation of undesirable by-products unless the synthetic operation follows stringent protection under an inert gas; 8 (2) aldehydes could undergo a decarbonylation reaction under harsh reaction conditions such as high temperature, which results in low product yields; 9 (3) some aldehydes including heteroaryl ones are of high cost or not readily available; the method for variation of products is hence restricted. On the basis of these facts, the search for readily available, inexpensive and stable alternatives of aldehydes would provide a new avenue for the synthesis of aryl substituted 1,3,5-triazines and is of high importance.…”

Section: Introductionmentioning

confidence: 99%

An efficient ruthenium-catalyzed dehydrogenative synthesis of 2,4,6-triaryl-1,3,5-triazines from aryl methanols and amidines

et al. 2014

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By using [RuCl2(p-Cymene)]2/Cs2CO3 as an efficient catalyst system, the readily available, inexpensive aryl methanols were firstly employed for dehydrogenative synthesis of aryl substituted 1,3,5-triazine derivatives. Due to the inherent stability of alcohols in contrast with aldehydes, our synthetic protocol is adaptable to a broad substrate scope, there is no need for stringent protection during the whole operation process, and it has the potential to prepare valuable products that are currently inaccessible or challenging to prepare using conventional methods. It is a significantly important complement to the conventional synthetic methodologies.

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Oxidation of aromatic aldehydes with potassium bromate–bromide reagent and an acidic catalyst

Cited by 14 publications

References 13 publications

Synthesis of functionalized pyrimidouracils by ruthenium‐catalyzed oxidative insertion of (hetero)aryl methanols into N‐uracil amidines

Synthesis of functionalized pyrimidouracils by ruthenium‐catalyzed oxidative insertion of (hetero)aryl methanols into N‐uracil amidines

Synthesis of Amidines and Its Application to Pyrimidouracil Synthesis

An efficient ruthenium-catalyzed dehydrogenative synthesis of 2,4,6-triaryl-1,3,5-triazines from aryl methanols and amidines

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