Isoindoline

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Isoindoline
3D representation of isoindoline
3D representation of isoindoline
Names
Preferred IUPAC name
2,3-Dihydro-1H-isoindole
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.156.955 Edit this at Wikidata
  • 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
  • c1cccc2c1CNC2
Properties
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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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. lenalidomide and pazinaclone.[3]

The drug lenalidomide contains the substructure isoindoline (red)

Substituted isoindolines

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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]

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References

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  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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