Palladium-Catalyzed Arylation and Heteroarylation of Azolopyrimidines

Mendiola, Javier; Castellote, Isabel; Alvárez‐Builla, Julio; Fernández‐Gadea, Javier; Gómez, and Antonio; Vaquero, Juan J.

doi:10.1021/jo051848e

Cited by 18 publications

(4 citation statements)

References 31 publications

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“…Only a limited amount of approaches have been developed for the synthesis of bicyclic pyrrole derivatives. , After efficaciously synthesizing 2-aminopyrroles from EDAMs, we continued to probe the scope of the tandem reaction.…”

Section: Resultsmentioning

confidence: 99%

Cascade Reaction of Morita–Baylis–Hillman Acetates with 1,1-Enediamines or Heterocyclic Ketene Aminals: Synthesis of Highly Functionalized 2-Aminopyrroles

Liu

Cao

et al. 2019

J. Org. Chem.

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A new strategy for the construction of two kinds of fully substituted pyrroles, including 2-aminopyrroles and bicyclic pyrroles from Morita–Baylis–Hillman (MBH) acetates with 1,1-enediamines (EDAMs), or heterocyclic ketene aminals (HKAs) via base-promoted tandem Michael addition, elimination, and aromatization sequence has been developed, affording the expected products in moderate to excellent yields. This methodology is a highly efficient, concise way to access 2-aminopyrroles or bicyclic pyrroles with diversity in molecular structures from accessible building blocks under moderate reaction conditions.

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Section: Resultsmentioning

confidence: 99%

Cascade Reaction of Morita–Baylis–Hillman Acetates with 1,1-Enediamines or Heterocyclic Ketene Aminals: Synthesis of Highly Functionalized 2-Aminopyrroles

Liu

Cao

et al. 2019

J. Org. Chem.

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“…For this process, a CH cleavage via a concerted metalation-deprotonation in the presence of carbonate as an intramolecular base was proposed as the mechanism [20]. In the case of the electron rich TAP, a palladium-catalyzed electrophilic aromatic substitution mechanism, previously reported for azole compounds, is considered to be more likely [21,22]. The C4 and C6 positions also proved to be the nucleophilic sites in the reaction with benzenediazonium salt [17].…”

Section: Synthesismentioning

confidence: 91%

Palladium-Catalyzed Arylations towards 3,6-Diaryl-1,3a,6a-triazapentalenes and Evaluation of Their Fluorescence Properties

Wang,

Opsomer,

de Jong

et al. 2024

Molecules

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Methyl 4-(1,3a,6a-triazapentalen-3-yl)benzoate (TAP1) shows interesting properties as a small molecule fluorophore. In the search for post-functionalization methods, palladium-catalyzed arylation reactions were demonstrated. Direct CH arylation reactions of TAP1 with various aryl halides resulted in 3,6-diaryltriazapentalenes TAP4, although mostly in poor yields. Bromination of TAP1 followed by Suzuki coupling, on the other hand, requires a more delicate procedure, but gave arylated products with the same regiochemistry (TAP4) in moderate to good yields. The structure of 6-phenyltriazapentalene TAP4a was confirmed by crystallographic analysis. In addition, the effect of the C6 arylation on the fluorescent properties of 3-aryl-1,3a,6a-triazapentalenes was studied in dichloromethane at room temperature and in 2-methyltetrahydrofuran at 77K, while the photophysical properties of two saponified derivatives were measured in acetonitrile.

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“…213 3-Furylboronic acids have also been used in this type of reaction, for instance, in the coupling to a 6-chloropurine ribonucleoside in the search for compounds with anti-HCV or cytostatic activity. 214 In addition, benzofurylboronic acids behave similarly to their non-benzocondensated counterparts, some recent examples of their use in Suzuki-Miyaura couplings being the synthesis of a precursor of the antimalarial machaeriol B, 215 sulfamide HIV-1 protease inhibitors, 216 antifungal dihydrofuranones, 217 heteroarylated azolopyrimidines 218 …”

Section: Scheme 31mentioning

confidence: 99%