Site-selective synthesis of arylated pyridines by Suzuki–Miyaura reactions of 2,3,5,6-tetrachloropyridine

Reimann, Stefan; Ehlers, Peter; Parpart, Silvio; Surkus, Annette‐Enrica; Spannenberg, Anke; Langer, Peter

doi:10.1016/j.tet.2015.05.114

Cited by 23 publications

(17 citation statements)

References 52 publications

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“…Various reaction conditions were tested, including the solvent, type of base, palladium catalyst, and material ratio [18]. Each condition was optimized during the synthesis processes, and single-factor experiments were carried out to determine the most effective conditions starting from 5-bromotetrandrine (Table 1).…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of new tetrandrine derivatives and their antitumor activities

Xiao

Yang

et al. 2016

Journal of Asian Natural Products Research

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A series of tetrandrine derivatives were designed and synthesized using Suzuki coupling reaction. Eleven targeted compounds with over 50% inhibition against HL60 and A549 human cancer cell lines at 10 μM were further evaluated for the in vitro antitumor activities by MTT or SRB assay. The biological results revealed that some compounds exhibited potent antitumor activities. Thiophene derivative 6 and acetylphenyl derivative 5 were the most active ones against HL60 and A549 cell lines, with IC50 values less than 5 μM, which thus could be considered as useful candidate for further development of new antitumor agents.

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Section: Resultsmentioning

confidence: 99%

Design and synthesis of new tetrandrine derivatives and their antitumor activities

Xiao

Yang

et al. 2016

Journal of Asian Natural Products Research

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“…The optimal conditions vary slightly from those disclosed recently to affect the Suzuki-Miyaura reaction of halopyridines with boronic acids (entry 4), 15 but the differences have a dramatic impact on the reaction. Empirical studies with different palladium sources and solvents revealed a beneficial effect derived from the use of a Pd(OAc) 2 pre-catalyst and solvation with 4:1 dioxane:water (entries 4–8).…”

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confidence: 80%

Exhaustive Suzuki–Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters

2017

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“…Also they have been identified as novel IKK-β inhibitors [4], A2A adenosine receptor antagonists [6] and potent inhibitor of HIV-1 [8]. Among pyridine derivatives sorfenib and nilotnib are used as anticancer drug against a panel of cell lines, namely; the liver cancer line [9][10] (Fig 1). in the presence of ammonium acetate at 100 ο C for five hours.…”

Section: Introductionmentioning

confidence: 99%

Conventional and Microwave Synthesis of some new pyridine derivatives and evaluation their antimicrobial and cytotoxic activities.

2018

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T HE NEWLY synthesized compounds based on 2-amino-6-(2,4-dimethoxyphenyl)-4-(4-methoxyphenyl)nicotinonitrile 1. The reactivity of pyridine derivative 1 was studied towards different reagents by its reaction with malononitrile, 2-(4-chlorobenzylidene) malononitrile, ethyl cyanoacetate, cyano acetic acid, m-nitro benzaldehyde, sodium azide, formamide, acetic anhydride and/or acetic anhydride/H 2 SO 4 to give compounds 2-5,7, 10-13, respectively. The reaction of 5 with acetyl acetone gave the bipyridine derivative 6, while reaction of compound 7 with chloroacetyl chloride and phenacyl bromide gave the azetidinone derivatives 8 and 9. The formimidate 14 were obtained via reaction of compound 1 with triethylorthoformate, while reaction of 14 with phenylene diamine and/or acetamide gave the formimidamide and pyridopyrimidine derivatives 15 and 16 respectively. Compound 1 was also allowed to react with urea, thiourea, phthalic anhydride, succinic anhydride, benzoyl chloride, chloroacetonitrile, chloroacetyl chloride, p-toluenesulfonylchloride and ethyl bromoacetate to give compounds 17a,b-24. Reaction of compound 1 with dichloro reagents in 1:1 ratio gave the bicyclic derivatives 25a-c, while its reaction with oxalyl chloride, dichloro and tetrachlorobenzoquinone derivatives, and/or dichloronaphthoquinone gave the imidazopyridine derivatives 26-29. Reaction of compound 29 with o-phenylenediamine in 1:2 ratio afforded the di-condenesed product 30 while, reaction of compound 1 with dichlororeagents in 1:2 ratio gave the polyalkyl derivatives 31a-b. The newly synthesized compounds were characterized by IR, 1 H-NMR, 13 C-NMR and mass spectra. On the other hand the antimicrobial and anticancer activities of some of the newly synthesized compounds were studied and evaluated.

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Site-selective synthesis of arylated pyridines by Suzuki–Miyaura reactions of 2,3,5,6-tetrachloropyridine

Cited by 23 publications

References 52 publications

Design and synthesis of new tetrandrine derivatives and their antitumor activities

Design and synthesis of new tetrandrine derivatives and their antitumor activities

Exhaustive Suzuki–Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters

Conventional and Microwave Synthesis of some new pyridine derivatives and evaluation their antimicrobial and cytotoxic activities.

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