Chemistry:Isoindoline

Isoindoline

Names
Preferred IUPAC name 2,3-Dihydro-1H-isoindole
Identifiers
CAS Number	496-12-8
3D model (JSmol)	Interactive image
ChemSpider	373951
PubChem CID	422478
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
SMILES c1cccc2c1CNC2
Properties
Chemical formula	C8H9N
Molar mass	119.167 g·mol−1
Except where otherwise noted, data are 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. 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.

Substituted isoindolines

1-Substituted isoindolines and isoindolinones are chiral. Isoindolylcarboxylic acid and 1,3-disubstituted isoindolines are constituents of some pharmaceuticals and natural products. Isoindolines 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.

Related compounds

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