Pd-Catalyzed highly selective and direct <i>ortho</i> C–H arylation of pyrrolo[2,3-<i>d</i>]pyrimidine derivatives

Zhou, Jing; Mao, Zhengtong; Pan, Haokun; Zhang, Xingxian

doi:10.1039/c9qo01312a

Cited by 20 publications

(3 citation statements)

References 41 publications

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“…Because directed C–H functionalization is often employed to introduce aromatic groups, ,, we also evaluated the effect of biaryl substituents on the pyrimidine contraction. These results are summarized in Figure A.…”

Section: Resultsmentioning

confidence: 99%

Skeletal Editing of Pyrimidines to Pyrazoles by Formal Carbon Deletion

2022

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A method for the conversion of pyrimidines into pyrazoles by a formal carbon deletion has been achieved guided by computational analysis. The pyrimidine heterocycle is the most common diazine in FDA-approved drugs, and pyrazoles are the most common diazole. An efficient method to convert pyrimidines into pyrazoles would therefore be valuable by leveraging the chemistries unique to pyrimidines to access diversified pyrazoles. One method for the conversion of pyrimidines into pyrazoles is known, though it proceeds in low yields and requires harsh conditions. The transformation reported here proceeds under milder conditions, tolerates a wide range of functional groups, and enables the simultaneous regioselective introduction of N-substitution on the resulting pyrazole. Key to the success of this formal one-carbon deletion method is a room-temperature triflylation of the pyrimidine core, followed by hydrazine-mediated skeletal remodeling.

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Section: Resultsmentioning

confidence: 99%

Skeletal Editing of Pyrimidines to Pyrazoles by Formal Carbon Deletion

2022

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“…Because directed C−H functionalization is often employed to introduce aromatic groups, 15,29,30 we also evaluated the effect of biaryl substituents on the pyrimidine contraction. These results are summarized in Figure 4A.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Correction to “Skeletal Editing of Pyrimidines to Pyrazoles by Formal Carbon Deletion”

Bartholomew¹,

Carpaneto²,

Sarpong³

2023

J. Am. Chem. Soc.

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Metrics & MoreArticle Recommendations * sı Supporting Information Supporting Information. In the published version, partial tabulation and spectral information for compounds 3a, 8b, 17, 20, 23, and S54 were missing because an earlier version of the Supporting Information was inadvertently published. A new version of the Supporting Information that contains all of this information is provided herein. ■ ASSOCIATED CONTENT* sı Supporting InformationThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.2c13180. Experimental procedures, characterization data, spectra for all new compounds, crystallographic data and Cartesian coordinates of DFT-optimized structures, and computational details (corrected) (PDF)

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“…Meanwhile, the tensile and flexural strengths were maintained with the introduction of TFAD. The above system shows that the introduction of nitrogen-rich groups can effectively improve the mechanical properties of EPs and have good thermal stability. , Pyrimidines, as nitrogen-containing organic heterocyclic compounds, have been widely used for manufacturing materials and medicines. − However, there are only a few reports on the use of pyrimidines for constructing efficient flame retardants.…”

Section: Introductionmentioning

confidence: 96%

P/N Flame Retardant Based on a Pyrimidine Ring for Improving the Flame Retardancy, Mechanical Properties, and Smoke Suppression of Epoxy Resin

Mao

et al. 2023

ACS Appl. Polym. Mater.

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A P/N flame-retardant TBD based on a pyrimidine ring was devised and developed by reacting 2,4,6-triaminopyrimidine, benzaldehyde, and 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide to create a less toxic, low-smoke, and mechanically improved the flame-retardant epoxy resin (EP). The EP modified using TBD exhibited good transparency, which was attributed to the outstanding compatibility of TBD with the EP. With a phosphorus content of only 0.65%, EP/TBD10 passed the V-0 rating of the UL-94 test, and the limited oxygen index increased from 27.1% (pure EP) to 38.1%. In the cone calorimetry test (CCT), the peak heat release rate and the total heat release decreased by 34.9 and 45.7%, respectively, compared to pure EP. In addition, the modified cured EP exhibited good mechanical properties owing to the action of rigid groups and the formation of hydrogen bonds, and the tensile strength and modulus as well as the flexural strength and modulus of the samples were improved. In the smoke density test, EP/TBD20 received the ratings of HL1 and HL2 in D s(4) and VOF4, respectively, according to EN45545-2. All results indicate that TBD is an efficient flame retardant that can enhance the flame retardancy and mechanical properties of the curing EP and reduce its smoke density, making it suitable for use in the rail transportation industry.

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Pd-Catalyzed highly selective and direct ortho C–H arylation of pyrrolo[2,3-d]pyrimidine derivatives

Abstract: Pd-Catalyzed one-pot direct ortho C–H arylation of pyrrolo[2,3-d]pyrimidine derivatives is reported. This protocol provides a variety of biphenyl-containing pyrrolo[2,3-d]pyrimidines in good to excellent yields.

Cited by 20 publications

References 41 publications

Skeletal Editing of Pyrimidines to Pyrazoles by Formal Carbon Deletion

Skeletal Editing of Pyrimidines to Pyrazoles by Formal Carbon Deletion

Correction to “Skeletal Editing of Pyrimidines to Pyrazoles by Formal Carbon Deletion”

P/N Flame Retardant Based on a Pyrimidine Ring for Improving the Flame Retardancy, Mechanical Properties, and Smoke Suppression of Epoxy Resin

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