Cyanoethylation of the salts of cyanoguanidine in aprotic solvents

Aleksandrowicz, Piotr; Bukowska, Maria; Maciejewski, Mieczysław; Prejzner, J.

doi:10.1139/v79-419

Cited by 5 publications

(3 citation statements)

References 4 publications

(4 reference statements)

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“…Similar ylidene formation by the addition of α,β-unsaturated nitriles to active methylene reagents has been observed earlier in several reactions [101,250], as shown in Scheme 142. A variety of pyrimidine synthesis, utilizing nitriles as starting components has been reported [291,292,[304][305][306][307][308]. Enaminonitriles 403 and 404 react with trichloro-acetonitrile to yield the corresponding pyrimidine derivatives 405 and 406, respectively [106,229,309], as shown in Scheme 144.…”

Section: Scheme 138mentioning

confidence: 99%

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Elgazwy¹

2013

Organic Chem Current Res

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including purines [7,8], pyrimidines [9], pyrazines [10] (some which are widely employed in the fluorescent dye industry [11]), imidazoles [12], biphenylenes [13], porphyrazines (which have great potential in optical sensor technology) [14] and diimines that are used as catalysts [15]. This review highlights the alkenyl nitrile chemistry with the focus on the utility of heterocyclic compounds. The synthesis and chemistry of the highly strained aryl nitrile is also briefly reviewed [16]. Heterocycles are ubiquitous in all kind of compounds of interest, and among all the possible synthetic methods of achieving their introduction into an structure, probably the use of a alkenyl nitrile analogue is the most direct one. The present review deals with the generation and synthetic uses of alkenyl nitriles and aryl nitriles formed in heterocyclic synthesis, and can be considered as an update of our revision published in 2007 on this topical [17]. Therefore, only references published from the second quarter of 2003 until the third quarter of 2010 are included, and the same restrictions to the literature coverage applied. Thus, only heterocycles compounds which are found applicability are considered. As previously, the present review is organized by the type of ring members and subdivided by the type of heterocycles fused compounds, including methods for their preparation and their synthetic uses. New developments in the utilities of some alkenyl nitriles in heterocyclic synthesis are reviewed. General synthetic routes based on the utilization of alkenyl nitriles of active imines are discussed. The major methods and modifications are analyzed [18-21]. In this review, which covers the literature up to date, we describe the new and improved methods for the construction of the skeletons, with a particular emphasis on the four, five and six membered ring of heterocyclic compounds. Some of these procedures have clear technical advantages over older methods in terms of yield and versatility, but do not employ new chemistry in the construction of the ring systems. The

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Section: Scheme 138mentioning

confidence: 99%

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Elgazwy¹

2013

Organic Chem Current Res

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“…As early as in 1979, an attempt was made by us in consideration of cyanoethyl derivatives of cyanoguanidine as monomers to obtain polyguanamines [31]. With this in mind, we have been pursuing a set of two reactions, whose effectiveness is theoretically as high as 4 reactive sites from one.…”

Section: Reprintsmentioning

confidence: 99%

Guanamine Dendrimerization

Maciejewski

Bednarek²,

Janiszewska

et al. 2000

Journal of Macromolecular Science, Part A

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A synthesis of dendrimers and hyperbranched polymers by using cycloaddition of cyanoguanidine to nitriles and cyanoethylation reaction is reported. Both reactions proceeded in the presence of a basic catalyst (alkaline hydroxides and Triton B, respectively). ORDER REPRINTSThe guanamine dendrimerization process has been carried out up to 4 th generations ended with cyano or amine groups. Intermediates and product substances, as well as by-products were identified by FT-IR, 1 H and 13 C NMR, MS, FIB-MS, and elemental analysis. Hyperbranched polymers were characterized by gel permeation choursomatography (GPC). Polyguanamine dendrimer (PGD) molecules exhibited expanded form in dimethylacetamide solution and low polydispersity (1.12-1.26). Observed contraction of the macromolecules was growing towards higher generations reaching an extreme at generation 4. The degree of branching of the products were within the range of 0.81-0.87 on the 0-1 scale.Decyanoethylation, hydrolysis, and intramolecular cyclization, as side reactions, were observed on the cycloaddition steps of dendrimerization. Some main stream dendrimerization products, i.e., tetrakis [2-(2,4-diamino-1,3,5-triazin-4-yl)ethyl]2,4-diamino-6-phenyl-1,3,5-triazine and 2,2,6,6-tetrakis[2-(2,4-diamino-1,3,5-triazin-6-yl)ethyl]cyclohexanone as well as by-products, i.e., 2,6,6-tris[2-(2,4-diamino-1,3,5-triazin-6-yl)ethyl] cyclohexanone, 2,6,6-tris(2-cyanoethyl)cyclohexanone and a dilactam have been isolated as new compounds. Spectral data for N 2 N 2 N 4 N 4 -tetrakis(2-cyanoethyl)-6-phenyl-1,3,5-triazine, 2,2,-6,6-tetrakis(2-cyanoethyl)cyclohexanone, 1,1,1-tris(2-cyanoethyl)propanone-2 and 1,1,1-tris[2-(2,4-diamino-1,3,5-triazin-6yl)ethyl]propanone-2 have been complemented. 754 MACIEJEWSKI ET AL.

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“…There are several reports involves the synthesis of 2-cyanoiminopyrimidines by (i) Multicomponent reaction of 1,3-dicarbonyl compounds, cyanamides and aromatic aldehydes 10 (ii) condensation of cyanoguanidine with acrylic acid derivatives 11 . The multicomponent reaction of aromatic aldehydes, cyanoguanidine and acetyl compounds give the corresponding pyrimidin-2-ylcyanamide 12 (Figure 1) instead of dihydrocyanoiminopyrimidines.…”

Section: Introductionmentioning

confidence: 99%

A New Approach to the Synthesis of Cyanamide: 2-Cyanoimino-4-aryl-6-(naphthalen-2-yl)-3,4-dihydro-1H-pyrimidines and their Antimicrobial Screening

2015

Chem Sci Trans

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A series of cyanoiminopyrimidines were synthesized by the reaction of 1-(2-naphthyl)-3arylprop-2-en-1-ones with cyanoguanidine in the presence of sodium hydroxide in ethanol. The mechanism involves the 1,4 or 1,2-addition of cyanoguanidine to α,β-unsaturated ketone, heterocyclisation and subsequent tautomeric change of formed adduct with loss of water. All the newly synthesized compounds were characterized by IR and NMR spectral studies. The in vitro antimicrobial screening of synthesized compounds showed the significant antifungal activities compared to the standard fluconazole.

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Cyanoethylation of the salts of cyanoguanidine in aprotic solvents

Cited by 5 publications

References 4 publications

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

The Chemistry of Alkenyl Nitriles and its Utility in Heterocyclic Synthesis

Guanamine Dendrimerization

A New Approach to the Synthesis of Cyanamide: 2-Cyanoimino-4-aryl-6-(naphthalen-2-yl)-3,4-dihydro-1H-pyrimidines and their Antimicrobial Screening

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