Isoindoline

Isoindoline
Names
	IUPAC name 2,3-dihydro-1H-isoindole
Identifiers
CAS Number	496-12-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	373951;
ECHA InfoCard	100.156.955
PubChem CID	422478;
CompTox Dashboard (EPA)	DTXSID20964291 ;
	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).

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. 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.^[4]^[5]^[6]

Related compounds

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

References

^ Isoindoline
^ Isoindoline
^ Speck Klaus; Magauer Thomas "The chemistry of isoindole natural products" Beilstein journal of organic chemistry 2013, vol. 9, pp. 2048-78. doi:10.3762/bjoc.9.243
^ Pandey, G.; Varkhedkar, R.; Tiwari, D (2015) Efficient Access to Enantiopure 1,3-disubstituted Isoindolines from Selective Catalytic Fragmentation of Original Desymmetrized Rigid Overbred Template, Org. Biomol. Chem., DOI: 10.1039/C5OB00229J
^ A Facile Access to Enantioenriched Isoindolines via One-Pot Sequential Cu(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition/Aromatization DOI: 10.1021/ol302987h
^ Asymmetric organocatalytic formal double-arylation of azomethines for the synthesis of highly enantiomerically enriched isoindolines DOI: 10.1039/B917246G

[1] Isoindoline

[2] Isoindoline

[3] Speck Klaus; Magauer Thomas "The chemistry of isoindole natural products" Beilstein journal of organic chemistry 2013, vol. 9, pp. 2048-78. doi:10.3762/bjoc.9.243

[4] Pandey, G.; Varkhedkar, R.; Tiwari, D (2015) Efficient Access to Enantiopure 1,3-disubstituted Isoindolines from Selective Catalytic Fragmentation of Original Desymmetrized Rigid Overbred Template, Org. Biomol. Chem., DOI: 10.1039/C5OB00229J

[5] A Facile Access to Enantioenriched Isoindolines via One-Pot Sequential Cu(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition/Aromatization DOI: 10.1021/ol302987h

[6] Asymmetric organocatalytic formal double-arylation of azomethines for the synthesis of highly enantiomerically enriched isoindolines DOI: 10.1039/B917246G

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