Cyanamide: a convenient building block to synthesize 4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine systems via a multicomponent reaction

Hulme, Roger; Zamora, O. D. P.; Mota, E. J.; Pasten, M. A.; Contreras-Rojas, R.; Miranda, René; Valencia-Hernández, Ignacio; Correa‐Basurto, José; Trujillo‐Ferrara, José G.; Delgado, Francisco

doi:10.1016/j.tet.2008.01.087

Cited by 37 publications

(23 citation statements)

References 48 publications

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“…As a result of theoretical DFT calculation about the energies of tautomers indicates that the presence of NH protons as in the pyrimidine ring is more favored for cyanoiminopyrimidine and not for other tautomers T-1 and T-2. The possibilities of tautomers with more stable form of synthesized cyanoiminopyrimidines were reported in earlier findings as same 18,19 .…”

Section: T-1 T-2 T-3mentioning

confidence: 61%

An Efficient Synthesis and In Vitro Antimicrobial Screening of 2-Cyanoimino -4-aryl-6-(1,1'-biphenyl-4-yl)-3,4-dihydro-1H-Pyrimidines

Swaminathan¹,

Namasivayam²

2018

Orient. J. Chem

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An efficient synthesis of 2-Cyanoimino-4-aryl-6-(1,1'-biphenyl-4-yl)-3,4-dihydro-1H-pyrimidines from stryl-4-biphenylketones and cyanoguanidine in presence of sodium hydroxide has been described. Cyanoguanidine serves as N-C≡N source for the construction of desired cyanoiminopyrimidines. The structural assignments of the titled products were done accordingly to their spectra like Mass, FT-IR, Proton and Carbon-13 NMR spectroscopy. The more stable tautomeric form was ascertained using computational frequency analysis. The tested microorganism profile of compounds exhibits significant antimicrobial activity.

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Section: T-1 T-2 T-3mentioning

confidence: 61%

An Efficient Synthesis and In Vitro Antimicrobial Screening of 2-Cyanoimino -4-aryl-6-(1,1'-biphenyl-4-yl)-3,4-dihydro-1H-Pyrimidines

Swaminathan¹,

Namasivayam²

2018

Orient. J. Chem

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“…Scheme 10 shows the following literature examples of [3 + 2 + 1] cycloadditions following the traditional mapping (red structure shown in Fig. 9): Biginelli [163–165], Shaabani [166], Martins [167], Khodaei [168], Saxena [169], Zhu [170], Zhu [171], Organ [172], Mizar [173], Schmidt [174], Ramalingan [175], Kappe [176], Hulme [177], Tu [178], Matache [179], Zhang [180], Singh [181], Hong [182], Lei [183], Shaabani [184], Tu [185], Han [186], Fang [187], and Zeng [188]. Scheme 11 shows the following literature examples of [3 + 2 + 1] cycloadditions following novel mappings (blue structures shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

A new paradigm for designing ring construction strategies for green organic synthesis: implications for the discovery of multicomponent reactions to build molecules containing a single ring

Andraos¹

2016

Beilstein J. Org. Chem.

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A new way of developing novel synthesis strategies for the construction of monocyclic rings found in organic molecules is presented. The method is based on the visual application of integer partitioning to chemical structures. Two problems are addressed: (1) the determination of the total number of possible ways to construct a given ring by 2-, 3-, and 4-component couplings; and (2) the systematic enumeration of those possibilities. The results of the method are illustrated using cyclohexanone, pyrazole, and the Biginelli adduct as target ring systems with a view to discover new and greener strategies for their construction using multicomponent reactions. The application of the method is also extended to various heterocycles found in many natural products and pharmaceuticals.

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“…Thiamine is a very important physiological molecule because it serves as a cofactor (in the form of thiamine diphosphate) for several enzymes involved primarily in carbohydrate catabolism. Thiamine is composed of pyrimidine and thiazole rings linked by a methylene bridge, whereas cyanamide can be utilized in pyrimidine synthesis (52). Hence, it is plausible to speculate that cyanamide could be utilized by Ddi2/3 in pyrimidine rings and further in thiamine synthesis.…”

Section: Discussionmentioning

confidence: 99%

Two Duplicated Genes DDI2 and DDI3 in Budding Yeast Encode a Cyanamide Hydratase and Are Induced by Cyanamide

Biss

et al. 2015

Journal of Biological Chemistry

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Background: DDI2 and DDI3 are two uncharacterized identical genes found in budding yeast. Results: They encode novel cyanamide hydratases and are massively induced by cyanamide. Their deletion causes cellular sensitivity to cyanamide. Conclusion:The two genes function in cyanamide detoxification and are tightly regulated. Significance: This is the first attempt to understand the duplicated gene cluster in budding yeast.

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Cyanamide: a convenient building block to synthesize 4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidine systems via a multicomponent reaction

Cited by 37 publications

References 48 publications

An Efficient Synthesis and In Vitro Antimicrobial Screening of 2-Cyanoimino -4-aryl-6-(1,1'-biphenyl-4-yl)-3,4-dihydro-1H-Pyrimidines

An Efficient Synthesis and In Vitro Antimicrobial Screening of 2-Cyanoimino -4-aryl-6-(1,1'-biphenyl-4-yl)-3,4-dihydro-1H-Pyrimidines

A new paradigm for designing ring construction strategies for green organic synthesis: implications for the discovery of multicomponent reactions to build molecules containing a single ring

Two Duplicated Genes DDI2 and DDI3 in Budding Yeast Encode a Cyanamide Hydratase and Are Induced by Cyanamide

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