Utilization of nitriles as the nitrogen source: practical and economical construction of 4-aminopyrimidine and β-enaminonitrile skeletons

Zhu, Yu; Li, Yinghua; Xiang, Shiqun; Fan, Weibin; Jiang, Jin; Huang, Deguang

doi:10.1039/c9qo00619b

Cited by 15 publications

(15 citation statements)

References 69 publications

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“…The bond lengths and bond angles of heterocyclic rings are comparable to those presented in the analogous compounds, 26 indicating the formation of pyrimidine cores and peripheral amidine function groups.…”

Section: Rsc Advances Papersupporting

confidence: 58%

“…1,25 We recently reported a simple and catalyst-free method for the synthesis of b-enaminonitriles and 4-aminopyrimidines by using aliphatic nitriles as electron donors and benzonitriles as electron acceptor (Scheme 2h). 26 However, the application of aliphatic nitriles and other types of aromatic nitriles (e.g. naphthyl, pyridyl, thienyl) as electron acceptors has not been concerned.…”

Section: Introductionmentioning

confidence: 99%

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Temperature controlled condensation of nitriles: efficient and convenient synthesis of β-enaminonitriles, 4-aminopyrimidines and 4-amidinopyrimidines in one system

Zhu

Xiang

et al. 2020

RSC Adv.

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Section: Rsc Advances Papersupporting

confidence: 58%

Section: Introductionmentioning

confidence: 99%

Temperature controlled condensation of nitriles: efficient and convenient synthesis of β-enaminonitriles, 4-aminopyrimidines and 4-amidinopyrimidines in one system

Zhu

Xiang

et al. 2020

RSC Adv.

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“…In contrast, the use of less amount of 1a, such as one equivalent or two equivalents, would decrease the yields down to 54% and 66% (entries 14-15), respectively. It has been shown that the strong base of EtONa and t BuOK et al would promote an extra transformation of phenylacetonitrile to β-enaminonitrile and/or 4-aminopyrimidine by mean of self-condensation (Zhu et al, 2019;Li et al, 2020), which would lead to the loss of the starting material of 1a unwillingly. In addition, the dioxygen atmosphere is crucial for the activation of nitromethane.…”

Section: Resultsmentioning

confidence: 99%

Copper(II)-Dioxygen Facilitated Activation of Nitromethane: Nitrogen Donors for the Synthesis of Substituted 2-Hydroxyimino-2-phenylacetonitriles and Phthalimides

Xiang

Fan

et al. 2021

Front. Chem.

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A simple and efficient method is explored for the synthesis of 2-hydroxyimino-2-phenylacetonitriles (2) and phthalimides (4), by using nitromethane as nitrogen donors. Both reactions are promoted by Cu(II) system with the participation of dioxygen as an oxidant. The scope of the method has been successfully demonstrated with a total of 51 examples. The flexible and diversified characteristics of reactions are introduced in terms of electronic effect, steric effect, position of substituted groups, and intramolecular charge transfer. Experimental studies suggest that the methyl nitrite could be a precursor in the path to the final products. A possible reaction mechanism is proposed, including the Cu(II)/O2-facilitated transformation of nitromethane to methyl nitrite, the base-induced formation of 2-hydroxyimino-2-phenylacetonitriles, and the base-dioxygen-promoted formation of phthalimides.

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“…Hence, economical and practical synthetic routes of 4-aminopyrimidines and β-enaminonitrile has immense utility in organic chemistry and pharmaceutical chemistry. The application of organonitriles as a supplemental source of nitrogen is an area of great scientific interest currently in the synthesis of 4-aminopyrimidine moieties [ 52 ].…”

Section: Synthetic Strategies Of Pyrimidinesmentioning

confidence: 99%

Synthetic Strategies of Pyrimidine-Based Scaffolds as Aurora Kinase and Polo-like Kinase Inhibitors

et al. 2021

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The past few decades have witnessed significant progress in anticancer drug discovery. Small molecules containing heterocyclic moieties have attracted considerable interest for designing new antitumor agents. Of these, the pyrimidine ring system is found in multitude of drug structures, and being the building unit of DNA and RNA makes it an attractive scaffold for the design and development of anticancer drugs. Currently, 22 pyrimidine-containing entities are approved for clinical use as anticancer drugs by the FDA. An exhaustive literature search indicates several publications and more than 59 patents from the year 2009 onwards on pyrimidine derivatives exhibiting potent antiproliferative activity. These pyrimidine derivatives exert their activity via diverse mechanisms, one of them being inhibition of protein kinases. Aurora kinase (AURK) and polo-like kinase (PLK) are protein kinases involved in the regulation of the cell cycle. Within the numerous pyrimidine-based small molecules developed as anticancer agents, this review focuses on the pyrimidine fused heterocyclic compounds modulating the AURK and PLK proteins in different phases of clinical trials as anticancer agents. This article aims to provide a comprehensive overview of synthetic strategies for the preparation of pyrimidine derivatives and their associated biological activity on AURK/PLK. It will also present an overview of the synthesis of the heterocyclic-2-aminopyrimidine, 4-aminopyrimidine and 2,4-diaminopyrimidine scaffolds, and one of the pharmacophores in AURK/PLK inhibitors is described systematically.

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Utilization of nitriles as the nitrogen source: practical and economical construction of 4-aminopyrimidine and β-enaminonitrile skeletons

Abstract: A highly practical and economical method for the synthesis of 4-aminopyrimidines and β-enaminonitriles from mixed organonitriles is reported.

Cited by 15 publications

References 69 publications

Temperature controlled condensation of nitriles: efficient and convenient synthesis of β-enaminonitriles, 4-aminopyrimidines and 4-amidinopyrimidines in one system

Temperature controlled condensation of nitriles: efficient and convenient synthesis of β-enaminonitriles, 4-aminopyrimidines and 4-amidinopyrimidines in one system

Copper(II)-Dioxygen Facilitated Activation of Nitromethane: Nitrogen Donors for the Synthesis of Substituted 2-Hydroxyimino-2-phenylacetonitriles and Phthalimides

Synthetic Strategies of Pyrimidine-Based Scaffolds as Aurora Kinase and Polo-like Kinase Inhibitors

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