Acylamidation

More recently, the Lewis acid promoted asymmetric 1,4-addition of trimethyl(2-propenyl)silane to chiral a,/ -unsaturated /V-acylamides has been published33. Lewis acid mediated reactions of trimethyl(2-propenyl)silanes with a,/I-unsatu rated AT-acyloxazolidinones or iV-enoylsultams show high chemical yield with good diastereomeric excess. The absolute configuration of the new asymmetric center is controlled by the nature of the Lewis acid used. 

In analogy, Ugi et al. reported on a lactam formation by running a one-pot three components reaction the condensation of L-lysine 7, isobutyraldehyde and methyl isocyanide led to the corresponding a-amino-c-caprolactam 9, but the yield was not given. The authors presumed either a nucleophilic substitution of the ester 8 as the primary Ugi product by the amino function of the side chain or, alternatively, the nucleophilic attack of the NH2-group on an intermediately formed 0-acylamide and a subsequent rearrangement (Scheme 1) [4]. 

Anilide herbicides are metabolized in plants via cleavage of acylamide moiety. 

Fatty acids, their glycerides and other esters, including fats, waxes and oils such as mineral and vegetable oils fatty alkylamines and acylamides. Alkaline earth metal or aluminium salts of fatty acids tend to leave deposits on machinery [536]. 

Unlike acylamides, sulphonamides react with biguanides to yield mainly open-chain compounds, but the biguanide structure is cleaved in... 

New types of fluorinated cyclopent[d]-3,l-oxazines and tetrahydro-4//-3,l-benzoxazines 180 and 181 were prepared (88IZV132 89TL-1987 91IZV1130, 91T5577). Cyclopentene, 1-methylcyclopentene, or 1,3-cyclohexadiene was reacted with a mixture of acetyl boron trifluoride and acetonitrile, resulting in the oxazines 180 and 181 regio- and stereospecifi-cally via acylamidation. 

The discovery of the sedative/hynoptic activity of derivatives of barbituric acid has led to very extensive dissections of that molecule. One outcome of this work is the realization that acylurea and acylamide derivatives often exhibit CNS depressant activity. A fair number of such molecules have been prepared that contain a succinimide or glutarimide pharmacophore. For example, Michael addition of cyanide to the stereochemically xmdefined cinnamate... 

The controlled photoelectrochemical oxidation of imides presents an interesting example of chemoselectivity. The photoinduced oxidation of lactams to imides, Eq. (22) and of N-acylamides to imides, Eq. (23) introduces oxygen into the organic substrate, but if the reaction is conducted in the presence of Cu(I), unsaturation is induced instead, Eq. (24)... 

Acylacyloxylation and Acylamidation (Addition of Oxygen, Carbon, or Nitrogen, Carbon)... 

Jancso, N. Desensitization with capsaicin and related acylamides as a tool for studying the function of pain receptors, edited by K. Lin, D. Armstrong, E.G. Prado, Pharmacology of Pain, 1968, Pergamon Press, Oxford, 33-55. 

Because of the lability of the carbonyl group of the acylamides and the stability of the rhodium-ammine bond, the use of RhCl3 with benzonitrile as solvent might be suggested. The use of RhCl3 in glycole in the presence of formaldehyde also appears to be quite practicable [70]. 

The Negative Ionizable feature was augmented to map on N-acylamides (0=C-NH-C=0) motif such as in Quis (Fig. 15.6a). 

Determine the number of cysteine residues by dividing the mass difference calculated for the acrylamide sample by 72.08 and 58.05 g/mol for the iodoacetamide sample (e.g., the mass shift of 432.49 g/mol for acylamide and 348.07 g/mol for iodoacetamide correspond to six cysteine residues in both cases, i.e., three disulfide bonds in the original sample). 

Thiazinones 39 undergo ring opening under very mild conditions (aqueous acetone, 25°C) to give A -acylamides of 3-mercaptoacrylic acid 226. But these compounds are unstable and afford TV-acylamides of 3-oxoacids if not quickly isolated from the reaction mixture (81H851) (Scheme 84). 

In our early work, esters of p-amidinobenzoic acid (8) were shown to behave as specific substrates of trypsin, as mentioned in Sect. 4.1. Esters 8 have the same molecular arrangement as normal-type substrates although they have a simplified structure lacking an asymmetric carbon and an a-acylamide group. In an extension of this investigation, we designed esters of an inverted structure, namely acyl derivatives of p-amidinophenol (46). 

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