Formaldehyde-Dimethylamine

Larsen, Scott D.

doi:10.1002/047084289x.rf019

Cited by 1 publication

(1 citation statement)

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“…The Mannich reaction introduces a C1 unit to various nucleophilic species through electrophilic aminomethylation. The (dimethylamino)methylation reaction with formaldehyde–dimethylamine or Eschenmoser’s salt is representative of the Mannich reaction. The resulting aminomethylated products are referred to as Mannich bases, which have established utility in organic syntheses owing to their ready accessibility and unique reactivity .…”

Section: Introductionmentioning

confidence: 99%

Substitution of the Dimethylamino Group in Gramines and One-Pot Cyclization to Tetrahydro-β-carbolines Using a Triazine-Based Activating Agent

et al. 2019

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A new method for the substitution of 3-[(dimethylamino)methyl]indoles (gramines) with malonate-based nucleophiles was developed using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) as the activating agent for the dimethylamino group. The reaction was completed in 1.5–6 h at room temperature in the presence of a tert-amine base and lithium salt. CDMT afforded superior results to methyl iodide, a common activating agent for the dimethylamino group in Mannich bases, particularly in the reactions of 1-substituted gramines. The reactivity of the possible intermediates, bis(indol-3-ylmethyl)dimethylammonium salts, was examined to obtain mechanistic insights on the reaction. This substitution method with CDMT enabled the sequential transformation of gramines: substitution with (N-alkylidene)aminomalonates followed by the Pictet–Spengler reaction under acidic conditions afforded 1,2,3,4-tetrahydro-β-carboline derivatives in one pot.

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Section: Introductionmentioning

confidence: 99%