Prajmalium

Álvarez, Julio L.; Vassort, Guy

doi:10.1111/j.1527-3466.1993.tb00197.x

Cited by 1 publication

(2 citation statements)

References 91 publications

(109 reference statements)

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“…Indoline motif is also an interesting substructure as demonstrated with Prajmaline 4 , an antiarrhythmic agent to treat cardiac disorders, [6] Eserine (Physostigmine) 5 , used to treat glaucoma and delayed gastric emptying, [7] or the compound 6 , a potent Cholesterol Ester Transfer Protein (CETP) Inhibitor [8] . (Figure 1)…”

Section: Figurementioning

confidence: 99%

“…[2] As representative examples, indole and indoline derivatives exhibit a broad spectrum of biological activities as highlighted in indole series by Arbidol 1, a drug with a broad antiviral spectrum against influenza A and B, [3] Ondansetron 2 used to prevent nausea and vomiting caused by cancer chemotherapy, radiation therapy or surgery, [4] or Fluvastatin 3, prescribed against hypercholes-terolemia and to prevent cardiovascular diseases. [5] Indoline motif is also an interesting substructure as demonstrated with Prajmaline 4, an antiarrhythmic agent to treat cardiac disorders, [6] Eserine (Physostigmine) 5, used to treat glaucoma and delayed gastric emptying, [7] or the compound 6, a potent Cholesterol Ester Transfer Protein (CETP) Inhibitor. [8] (Figure 1)…”

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confidence: 99%

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Selective Iron Catalyzed Synthesis of N‐Alkylated Indolines and Indoles

Tongdee

Cordier

et al. 2022

Chemistry A European J

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Whereas iron catalysts usually promote catalyzed C3‐alkylation of indole derivatives via a borrowing‐hydrogen methodology using alcohols as the electrophilic partners, this contribution shows how to switch the selectivity towards N‐alkylation. Thus, starting from indoline derivatives, N‐alkylation was efficiently performed using a tricarbonyl(cyclopentadienone) iron complex as the catalyst in trifluoroethanol in the presence of alcohols leading to the corresponding N‐alkylated indoline derivatives in 31–99 % yields (28 examples). The one‐pot, two‐step strategy for the selective N‐alkylation of indolines is completed by an oxidation to give the corresponding N‐alkylated indoles in 31–90 % yields (15 examples). This unprecedented oxidation methodology involves an iron salt catalyst associated with (2,2,6,6‐tetramethylpiperidin‐1‐yl)oxyl (TEMPO) and a stoichiometric amount of t‐BuOOH at room temperature.

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Section: Figurementioning

confidence: 99%