Carboxylic acid esters amides

The presence of electron withdrawing groups at the a position (R3) of the acrylate derivative increases the reactivity of the reagent toward conjugate addition, while substituents in the ( position (R4) tend to provide steric constraints that hinder carbon-carbon bond formation (Scheme 3). Of the various acrylate derivatives employed in these reactions, the most frequently used have electron withdrawing functionality such as a carboxylic acid, amide, ester, or nitrile group or a combination of these. Direct pyridone formation can be achieved primarily through the use of either a,(J acetylenic esters or acrylate derivatives with P substituents (Y = SR, OR, NR2) that eliminate under the reaction conditions. 

You will see a great example of this in Chapter 10 carboxylic acids, amides, esters, anhydrides... many functional groups, but all the same mechanisms. 

The polyketals can be readily derivatized. For example, aldehyde groups of an intermediate product of a polysaccharide oxidation can be converted into alcohol groups, amines, thioacetals, carboxylic acids, amides, esters, or thioesters. 

The earlier studies and the competition experiments [5b] with equivalent molar, enal, or enone 9-BBN (3-5% excess) reveal that enals or enones are selectively reduced to allylic alcohols (Eq. 25.9) in the presence of other organic functional groups such as nitro, halogen, epoxide, carboxylic acid, amide, ester, nitrile, sulfide, disulfide, sulfoxide, sulfone, tosylate, azo, etc. 

Activated Adds Chern. Soc. Rev. 1983, 12, 129 Angew. Chern. fnt. Ed. Engl. 1978, 17, 569. RC02F4 "activated acid" carboxylic acid derivative (ester, amide, etc.)... 

Anhydrides are reduced with relative ease. McAlees and McCrindle 20) established the following increasing order of difficulty for various carbonyls acid chlorides > aldehydes, ketones > anhydrides > esters > carboxylic acids > amides. Reduction may proceed by 1,2-addilion of hydrogen or by cleavage of an oxygen-carbonyl bond. If 1,2-addition to the carbonyl occurs, as in the presence of strong protic acids over palladium, 1,1-diesters are formed by acylation 26). 

The chemistry of carboxylic acids and esters The chemistry of the carbon-nitrogen double bond The chemistry of amides The chemistry of the cyano group The chemistry of the hydroxyl group (2 parts)... 

The Chemistry of Carboxylic Acids and Esters The Chemistry of the Carbon-Nitrogen Double Bond The Chemistry of the Cyano Group The Chemistry of Amides... 

Imides can be prepared by the attack of amides or their salts on acyl halides, anhydrides, and carboxylic acids or esters. The best synthetic method for the preparation of acyclic imides is the reaction between an amide and an anhydride at 100°C catalyzed by H2S04. When acyl chlorides are treated with amides in a2 l molar ratio at low temperatures in the presence of pyridine, the products are N,N-diacylamides, (RCO)3N. ... 

The reaction has been extended to ketones, carboxylic acids and esters (all of which couple a to the C=0 group), and amides (which couple a to the nitrogen) by running it in the presence of H2. ° Under these eonditions it is likely that the excited Hg abstracts H from H2, and that the remaining H- abstracts H from the substrate. 

Some pairs of functional groups such as alcohol, ester carboxylic acid, ester amine, amide and carboxylic acid, amide can be interconverted by simple reactions. When a member of these groups is the desired product or starting material, the other member should also be consulted in the text. 

Section 315 (Carboxylic Acid - Amide). Section 344 (Amide - Ester). 

Hydroxylation of long-chain carboxylic acids, amides, and alcohols—but not the esters or the corresponding alkanes—at the w-l, (0-2, and (o-3 positions by a soluble enzyme system from Bacillus megaterium (Miura and Fulco 1975 Narhi and Fulco 1986,1987). 

Alkylation of Aldehydes, Esters, Carboxylic Acids, Amides, and Nitriles... 

The classes of compounds that are conveniently considered together as derivatives of carboxylic acids include the acyl chlorides, carboxylic acid anhydrides, esters, and amides. In the case of simple aliphatic and aromatic acids, synthetic transformations... 

Pd-catalyzed carbonylation of heteroaryl halides provides a quick entry to heteroaryl carbonyl compounds such as heteroaryl aldehydes, carboxylic acids, ketones, esters, amides, a-keto esters and a-keto amides. In addition, Pd-catalyzed alkoxycarbonylation and aminocarbonylation are compatible with many functional groups, and therefore, are more advantageous than conventional methods for preparing esters and amides [78],... 

In Table 9, some conversions of heterocyclic carboxylic acids and esters are shown. The reactions involve amide formation, hydrolysis, and decarboxylation. 

A one-pot conversion of carboxylic acids into esters and amide derivatives from alcohols, amines or hydrazines has been reported [53], which involves the initial reaction of the acid with methane- or toluenesulphonyl chloride to yield a mixed anhydride. 

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