ChemInform Abstract: EFFICIENT SYNTHESIS OF 1,1′‐METHYLENEBIS‐1H‐PYRROLE DERIVATIVES

Gonzalez, Christina; Greenhouse, Robert

doi:10.1002/chin.198539191

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“…of alkylating agent, the N-isopropyl and N-benzyl products were formed in a 67 : 33 ratio. These observations led us to conclude that an S N 2 attack on the quaternary ammonium salts is more likely than the reverse Menschutkin forming benzyl chloride [9,10].…”

Section: Resultsmentioning

confidence: 93%

A Novel and Chemoselective Process ofN-Alkylation of Aromatic Nitrogen Compounds Using Quaternary Ammonium Salts as Starting Material

González-González

Vega

Monroy

et al. 2017

Journal of Chemistry

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The process of N-alkylation of several pyrroles, indoles, and derivative heterocycles is herein described, using quaternary ammonium salts as the source of an alkylating agent. These reactions were carried out on several heterocyclic rings with triethylbenzylammonium chloride or tetradecyltrimethylammonium bromide and an NaOH solution at 50%, leading to a chemoselective N-alkylated product and an average yield of 73%. This is an alternative process to the traditional benzylation and methylation of N-heterocycles with direct handling of alkyl halides.

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Section: Resultsmentioning

confidence: 93%