Methods of synthesis of nitrogen-containing heterocycles using ureas and related compounds

Бакибаев, А. А.; Yagovkin, A. Yu.; Vostretsov, S. N.

doi:10.1070/rc1998v067n04abeh000295

Cited by 23 publications

(14 citation statements)

References 93 publications

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“…Initially, 4-chloro aniline and diethyl chlorophosphate were heated at 80 °C in DMSO without any catalyst, but the reaction was unable to produce the product even after the prolonged heating for 48 h ( [12][13][14]. In the catalyst optimization studies with 2, 5 and 10 mol% of K 2 CO 3 , we obtained the yields were 68, 94 and 94 respectively (Table 1, Entries 12-14).…”

Section: Resultsmentioning

confidence: 82%

“…1) [12]. Recently, phosphoramidates have also been used in the field of plant hormone as abscisic acid (ABA) agonists that play role in plant growth regulators [13].Among literature methods, direct phosphorylation of different amines with phosphorus halides is one of the most attractive and synthetically accessible methods [14]. Coming to the reactivity, N-phosphorylation of the NH moiety of few N-heterocycles like indoles, imidazoles, and benzimidazole derivatives was reported with the similar reactivity as we expected in alkylations [15].…”

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confidence: 99%

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Potassium carbonate supported efficient synthesis of new diethyl arylphosphoramidates

et al. 2017

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of new diethyl arylphosphoramidatesKeywords: IntroductionPhosphoramidates have gained considerable interest in the last few decades as they have various applications in organic synthesis such as catalytic conversions like aldol and allylation reactions [1]. In addition to catalytic applications, N-arylphosphoramidates have been used as precursors for the synthesis of various heterocycles such as azetidines, aziridines, quinazolinediones and imines [2][3]. Beside this, they are also used to synthesize phosphate esters in nucleotides chemistry [4]. In analytical chemistry, phosphoramidates improve ionization efficiency and suppress matrix-related ion effects in MALDITOF mass spectrometry [5]. In medicinal chemistry, it is reported that phosphoramidates can be used as prodrug moieties to improve therapeutic potential of the parent drug [6]. Phosphoramidates have also served as surrogates for amide bond in the synthesis of peptide based protease inhibitors [7]. They represents some key structure in a number of biologically active natural products like agrocin 84 [8], phosmidosine (II) [9] and GS-6620 (III) [10]. They also form important pharmacophore of many biologically potent compounds e. g. sofosbuvir (IV) (FDA approved drug) used for the treatment of hepatitis C virus (HCV) [11], evofosfamidum (TH-302) (V) which is in clinical trials for cancer treatment (Fig. 1) [12]. Recently, phosphoramidates have also been used in the field of plant hormone as abscisic acid (ABA) agonists that play role in plant growth regulators [13].Among literature methods, direct phosphorylation of different amines with phosphorus halides is one of the most attractive and synthetically accessible methods [14]. Coming to the reactivity, N-phosphorylation of the NH moiety of few N-heterocycles like indoles, imidazoles, and benzimidazole derivatives was reported with the similar reactivity as we expected in alkylations [15]. These phosphoramidates featuring a P-N bond are used as pesticides in agriculture and prodrugs in therapeutic development, and for other synthetic applications [16]. Furthermore, they have been utilized as ligands for metal-catalyzed organic transformations, as flame retardants, and as labelling groups to improve sensitivity in mass spectroscopy [17]. The phosphorylation of a series of amines was studied under different conditions involving the application of the various methods. Our aim was to find the best set of conditions for the preparation of some of these phosphoramidates. ExperimentalGeneral: All reagents were obtained from Sigma-Aldrich and Alfa Aesar and were used directly without further purification. Melting points were recorded on Guna Digital Melting Point apparatus. IR spectra were recorded on Bruker AlphaEco ATR -FTIR interferometer with single reflection sampling module equipped with ZnSe crystal. Chemistry: Initially 0.127 mG (1 mmol) of 4-Chloro aniline (1a) was added to 0.144 mL (1 mmol) diethyl chlorophosphate (2) along with K 2 CO 3 (5 mol%) into a 50 mL round bottom flask in 8mL of DMSO. Then it i...

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Section: Resultsmentioning

confidence: 82%

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confidence: 99%

Potassium carbonate supported efficient synthesis of new diethyl arylphosphoramidates

et al. 2017

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“…Alkynyloxirane 74, which is readily obtainable from (R)-epichlorohydrin via two-step reaction [115], was converted into oxazolidinone 75, and the latter was then used for the synthesis of natural agelastatins A and B [116,117] [110,111] (Scheme 45). Interesting transformations of aryloxiranes on heating with urea under solvent-free conditions or in DMF were reported in [110].…”

Section: Synthesis Of 13-oxazolidin-2-ones From Isocyanates and Othementioning

confidence: 99%

“…Apart from isocyanates, carbon dioxide [108,109], urea [110,111], and 1,1′-carbonyldiimidazole [112][113][114] are used as carbonylating agents in the synthesis of 1,3-oxazolidin-2-ones. Patil et al [109] studied reactions of various epoxides (1,2-epoxypropane, phenyloxirane, epoxycyclohexane, epichlorohydrin, and 2,3-epoxypropyl ethers) with carbon dioxide in the presence of amino alcohols and Br -PPh 3 + -PEG-600-PPh 3 + Br -as efficient homogeneous catalyst.…”

Section: Synthesis Of 13-oxazolidin-2-ones From Isocyanates and Othementioning

confidence: 99%

Five-membered oxaza heterocyclic compounds on the basis of epoxides and aziridines

2011

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“…It might also be appropriate for a selective oxidization of the product obtained from selective monozonolysis. Cyclic non-conjugated polyolefinse-1,4-cyclohexadiene, 1,5-cyclooctadiene and 1,5,9-cyclododecatrieneare necessary for initiating the process used for developing the project (Preparation of the compound 1,5,9-cyclododecatriene) has thoroughly been described [8][9][10]. These polyolefins are all non-conjugated while their double bonds have approximately the same reactivity as that of the chemical reaction [11].…”

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Selective Mono-Ozonolysis of a Cyclic 1,5,9-Cyclododecatrien

Mustafa¹,

Chelebi²

2015

JESE-A

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Some unsaturated compounds with the required (Z,Z)-double bonds configuration are synthesized through controlled ozonolysis process of 1,5,9-cyclododecatriene by determining the necessary amount of ozone passing through to selectively guarantee the breakage of a double bond while leaving other two bonds as (Z,Z). The products were diagnosed by using NMR spectrum, infrared (IR) and mass spectrometer techniques. It is concluded that these products could widely be used in the synthesis of insect pheromones instead of insecticides and as useful intermediate compounds in many chemical reactions.

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Methods of synthesis of nitrogen-containing heterocycles using ureas and related compounds

Cited by 23 publications

References 93 publications

Potassium carbonate supported efficient synthesis of new diethyl arylphosphoramidates

Potassium carbonate supported efficient synthesis of new diethyl arylphosphoramidates

Five-membered oxaza heterocyclic compounds on the basis of epoxides and aziridines

Selective Mono-Ozonolysis of a Cyclic 1,5,9-Cyclododecatrien

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