Mechanochemical Diels-Alder Cycloaddition Reactions for Straightforward Synthesis of endo-Norbornene Derivatives

Zhang, Ze; Peng, Zhiwei; Hao, Mingfeng; Gao, Jiangang

doi:10.1055/s-0030-1259030

Cited by 33 publications

(20 citation statements)

References 2 publications

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“…Mechanochemistry has been used for a long time for the chemical and physicochemical transformations of inorganic materials to generate all states of aggregation produced by the effect of mechanical energy [ 40 ]. More recently, the mechanical energy has been used to synthesize organic molecules in milling devices [ 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 ].…”

Section: Introductionmentioning

confidence: 99%

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

et al. 2017

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A series of isoniazid derivatives bearing a phenolic or heteroaromatic coupled frame were obtained by mechanochemical means. Their pH stability and their structural (conformer/isomer) analysis were checked. The activity of prepared derivatives against Mycobacterium tuberculosis cell growth was evaluated. Some compounds such as phenolic hydrazine 1a and almost all heteroaromatic ones, especially 2, 5 and 7, are more active than isoniazid, and their activity against some M. tuberculosis MDR clinical isolates was determined. Compounds 1a and 7 present a selectivity index >1400 evaluated on MRC5 human fibroblast cells. The mechanism of action of selected hydrazones was demonstrated to block mycolic acid synthesis due to InhA inhibition inside the mycobacterial cell.

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Section: Introductionmentioning

confidence: 99%

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

et al. 2017

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“…7 Although the electron withdrawing group on C atom of ethylene can lower the activation barriers considerably, [8][9][10][11] the negative inductive effect of C=C on ethylene is so weak that the matching energy gap between the orbits of CPD is still large. The global electrophilicity of cyclopentadiene (CPD) is equal to 0.83eV, 12 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 whereas the global electrophilicity of butadiene is equal to 1.17eV.…”

Section: Introductionmentioning

confidence: 99%

Insights into the Diels–Alder Reactions between Cyclopentadiene and 1,3-Butadiene with High Temperature and High Pressure

Cao

Zhang

et al. 2015

Ind. Eng. Chem. Res.

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Synthesis of 5-vinyl-2-norbornene based on the Diels-Alder reactions of cyclopentadiene(CPD) generated from dicyclopentadiene(DCPD) and 1,3-Butadiene(BD) have been investigated in a continuous tube reactor under high temperature and high pressure. The experimental results show that the concentration of main product 5-vinyl-2-norbornene(VNB) increases with the increasing of reaction time at low reaction temperature. The elevated temperature greatly promotes the synthesis rate of both product VNB and its isomer cis-3a,4,7,7a-tetrahydroindene(THI)and tricyclopentadiene(TCPD), resulting in a mountain-shape curve of VNB concentration versus the reaction time. Particularly, it has been confirmed that the trimer (4,4a,4b,5,8,8a,9,9a-octahydro-1H-1,4-methanofluorene(OMF) should be prepared by direct reaction of BD with DCPD rather than by the reaction of CPD with VNB or THI. This comprehensive study can laid a solid foundation for the process optimization of VNB synthesis.

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“…Anhydride 20 underwent a Diels–Alder reaction with cyclopentadiene at ambient temperature to provide a mixture of endo and exo products in an 8:1 ratio ( Scheme 8 ). In comparison, it is known that maleic anhydride in analogous reactions affords exclusively the endo adduct [ 29 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes

Vida¹,

Václavík²,

Beier³

2016

Beilstein J. Org. Chem.

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SummaryOxidation of 3- and 4-pentafluorosulfanyl-substituted anisoles and phenols with hydrogen peroxide and sulfuric acid provided a mixture of SF5-substituted muconolactone, maleic, and succinic acids. A plausible mechanism for the formation of the aliphatic SF5 compounds was presented and their chemical reactivity was investigated. SF5-substituted para-benzoquinone was synthesized; its oxidation led to an improved yield of 2-(pentafluorosulfanyl)maleic acid. The reaction of SF5-substituted maleic anhydride and para-benzoquinone with cyclopentadiene afforded the Diels–Alder adducts. Decomposition of 3-(pentafluorosulfanyl)muconolactone in acidic, neutral and basic aqueous media was investigated and the decarboxylation of 2-(pentafluorosulfanyl)maleic acid provided 3-(pentafluorosulfanyl)acrylic acid.

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Mechanochemical Diels-Alder Cycloaddition Reactions for Straightforward Synthesis of endo-Norbornene Derivatives

Cited by 33 publications

References 2 publications

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

Insights into the Diels–Alder Reactions between Cyclopentadiene and 1,3-Butadiene with High Temperature and High Pressure

Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes

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