Isoindoline

Isoindoline

Names
IUPAC name 2,3-dihydro-1H-iso-indole
Identifiers
CAS Registry Number	496-12-8 [1]
ChemSpider	373951
InChI InChI=1S/C8H9N/c1-2-4-8-6-9-5-7(8)3-1/h1-4,9H,5-6H2 Key: GWVMLCQWXVFZCN-UHFFFAOYSA-N InChI=1/C8H9N/c1-2-4-8-6-9-5-7(8)3-1/h1-4,9H,5-6H2 Key: GWVMLCQWXVFZCN-UHFFFAOYAS
Jmol-3D images	Image
PubChem	422478
SMILES C1C2=CC=CC=C2CN1
Properties
Molecular formula	C8H9N
Molar mass	119.16 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Isoindoline is a heterocyclic organic compound with the molecular formula C₈H₉N.^[2] The parent compound has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. The compound's structure is similar to indoline except that the nitrogen atom is in the 2 position instead of the 1 position of the five-membered ring. Isoindoline itself is not commonly encountered, but several derivatives are found in nature and some synthetic derivatives are commercially valuable drugs, e.g. pazinaclone.^[3]

Substituted isoindolines

1-Substituted isoindolines and isoindolinones are chiral. Isoindolylcarboxylic acid and 1,3-disubstituted isoindolines are constituents of some pharmaceuticals and natural products. Iisoindolines can be prepared by 1,2-addition of a nucleophile onto a bifunctional ε-benzoiminoenoates followed by intramolecular aza-Michael reaction. Another route involves [3+2] cycloaddition of the azomethine ylides (e.g. CH₂)₂NR) to quinone in the presence of suitable catalysts. These methods have also been adapted to give chiral derivatives.^[4][5][6]

Related compounds

• 4,7-Dihydroisoindole
• Indoline
• Indole
• indene
• indoline
• benzofuran
• carbazole
• carboline
• isatin
• methylindole
• oxindole
• pyrrole
• skatole
• benzene

References