Carbon‐Carbon Alkylations with Amines and Ammonium Salts

Abstract

This chapter is a review of those reactions of compounds containing labile amino groups in which a carbon‐carbon bond is formed by amine replacement as, for example, in the alkylation of diethyl malonate by 1‐dimethylamino‐3‐butanone. Attention has been given primarily to reactions of amines prepared by the Mannich reaction (Mannich bases), but for comparison, analogous reactions of simpler quaternary ammonium salts have been included.

Double “Open and Shut” Transformation of γ-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds

“…Other organic bases such as i Pr 2 NEt, TMEDA, pyridine, DMAP, DBU, and DABCO were less effective than Et 3 N (runs 20–25). When inorganic bases such as K 2 CO 3 , Cs 2 CO 3 , and NaOH were used, ammonium bromide 1a was decomposed under the reaction conditions (runs 26–28) …”

Quaternary Ammonium Salts as Alkylating Reagents in C–H Activation Chemistry

“…Our approach was based on a very fundamental organic reaction, taught in every basic Organic Chemistry course: the Hofmann elimination . In this transformation a quaternary ammonium salt eliminates to the least substituted olefin and a tertiary amine (Scheme ).…”

Anti-malarial Activity of New Emodin Derivatives against Plasmodium falciparum Chloroquine Resistant Strain

“…To study the substituent effect on anthraquinone nucleus C-alkylated derivates 16-21 were prepared using Mannich reaction protocol [16][17][18][19][20] (Figure 2). …”