Isoindoline

Isoindoline
Names
IUPAC name
2,3-dihydro-1H-isoindole
Identifiers
496-12-8 [1]
3D model (Jmol) Interactive image
ChemSpider 373951
ECHA InfoCard 100.156.955
PubChem 422478
Properties
C8H9N
Molar mass 119.17 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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. 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]

References

  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
This article is issued from Wikipedia - version of the 9/22/2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.