7.8- Dihydro-5 -isoquinolinone

Isoquinol-4(l H)-one, 2,3-dihydro-synthesis, 2, 73 Isoquinolinones from isocoumarins, 3, 691 magnetic circular dichroism, 2, 129 synthesis,... 

The importance of proper immobilization of enzymes can be shown in the kinetic resolution of racemic a-acetoxyamides. This group of compounds is an important class of chemicals since they can be readily transformed into a-amino acids [17], N-methylated amino acids, and tripeptide mimetics [18], amino alcohols [19], 1,2-diols [20], 1,2-diamines [21], and enantiopure l,4-dihydro-4-phenyl isoquinolinones [22]. 

Solid-phase syntheses have become increasingly popular during the period of this review, with examples including the synthesis of 5,6,7,8-tetrahydro[l,6]naphthyridines from Meldrum s acids derived from /3-amino alcohols via Hantzsch condensation and cyclization with cyclative cleavage from the resin (using 70% trifluoroacetic acid (TFA)/dichloromethane (DCM) followed by 5% triethylamine/DCM) <1999S1951> and also of isoquinolinones and 5-oxo-5,6-dihydro-[l,6]naphthyridines <1995JOC5748>. 

The aromatization of 1,4-dihydro-3(2//)-isoquinolinones resulting in the corresponding 3(2//)-isoquinolinones is a known but not common proce-... 

Dihydro-3(2/7)-isoquinolinones (2 and its derivatives) (Section I) are structural isomers of the well-known dihydrocarbostyril and dihydro-isocarbostyril nitrogen heterocycles. However in 2, the —CO—NH— lactam group is separated from the aromatic benzene ring by two methylene groups. The effect of this is apparent in the limitation of synthetic methods and even more so in the differences in reactivity. 

Most possibilities and most examples in the syntheses of 1,4-dihydro-3(2//)-isoquinolinone (2) and its derivatives involve the cyclization of the corresponding arylacetic acid derivatives. The opportunity arises from the lactam structure of compound 2. With suitable reagents, different o-aminomethyl-, o-hydroxymethyl-, or o-chloromethyl-phenylacetic acid derivatives (25LA225 66JPR12 69CJC864 84JHC297) and o-hydroxymethyl phenylacetonitriles (85S114) can be cyclized. 

The N-methyl derivatives of 1 -aryl-1,4-dihydro-3(2//)-isoquinolinones (e.g., 54) can be lithiated in position 4 with butyllithium. The subsequent reaction, e.g., with p-nitrobenzaldehyde, gives the 4-p-nitrobenzylidene derivative. In this case, the condensation reaction is not followed by H-l rearrangement [86ACH(121)263]. 

In the case of, for example, l-aryl-l,4-dihydro-3(2tf)-isoquinolinones, iV-methylation takes place with dimethyl sulfate without difficulty [86ACH(121)263]. Acylation can also be carried out under the usual reaction conditions the derivatives 58, 59, and 60 are thus obtained in... 

Some 1 -aryl-1,4-dihydro-3(2//)-isoquinolinone derivatives can be converted to the corresponding isoindolinones by ring contraction oxidation with potassium permanganate [86ACH(121)237] of compounds 47 and 54 (Section III,B,1) and treatment with polyphosphoric acid (88ACH289) of several 4-hydroxyimino derivatives (19) (Section II,B,3) give the previously mentioned products. 

A number of 1-aryl derivatives of l,4-dihydro-3(2/f)-isoquinolinones proved to be anticonvulsants [77JMC1384 81ACH( 108)255 87ACH649]. Compound 82 with a basic side chain in position 4 of the 1 -aryl group has excellent effect as a new type of antiepileptic. Side chains containing a... 

Indole Iodide Isocyanide Isoquinoline (dihydro) (tetrahydro) Isoquinolinone Isoxazole P-Keto ester Ketone... 

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