Alkylation of amides

Secondary amines can be prepared by conversion of primary amines into sulfonamides, followed by N-alkylation and hydrolysis. Because sulfonamides are often difficult to hydrolyze, the N-alkylation of trifluoroacetamides has been investigated. Tri- 

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Among the substitution reactions involving the ring nitrogen atoms of the pteridine nucleus, alkylations of amide functions are preeminent. Under base-catalyzed conditions it is usually the nitrogen atom adjacent to the carbonyl function which is substituted... 

General procedure for alkylation of amidic and thioamidic heterocyclic systems... 

The potentially tautomeric 127/-quinoxalino[2,3-6]benzo-1,4-thiazines are alkylated at either the 11- or 12-positions [100] in a ca. 3 7 ratio (Scheme 5.24) under liquiddiquid two-phase conditions, analogous to those employed for the alkylation of amidic heterocycles. 

Alkylation of Amide Enolates Steric Hindrance vs. Electronic Control... 

In contrast to the many examples dealing with esters (see Section 1.1.1.3.2.), there are few examples in the literature of alkylations of amide enolates where the steric course is governed by the configuration of chiral units on the carbon side of the starting amide, i.e., substrate control by C-chirality. It is likely, however, that amide alkylations of this type will emerge as a very useful procedure since amide enolates are easy to prepare and usually, in contrast to some esters, provide very high ratios of syn- to a / -enolate. 

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