Isoindoline

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title: "Isoindoline" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["isoindolines"] topic_path: "general/isoindolines" source: "https://en.wikipedia.org/wiki/Isoindoline" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| verifiedrevid = 382025399 | ImageFileL1 = Isoindoline numbering.svg | ImageSizeL1 = | ImageFileR1 = Isoindoline3d.png | ImageSizeR1 = | ImageNameR1 = 3D representation of isoindoline | PIN = 2,3-Dihydro-1H-isoindole | Section1 = {{Chembox Identifiers | CASNo = 496-12-8 | CASNo_Comment = | PubChem = 422478 | ChemSpiderID = 373951 | SMILES = c1cccc2c1CNC2 | InChI = 1/C8H9N/c1-2-4-8-6-9-5-7(8)3-1/h1-4,9H,5-6H2 | InChIKey = GWVMLCQWXVFZCN-UHFFFAOYAS | StdInChI = 1S/C8H9N/c1-2-4-8-6-9-5-7(8)3-1/h1-4,9H,5-6H2 | StdInChIKey = GWVMLCQWXVFZCN-UHFFFAOYSA-N | Section2 = {{Chembox Properties | C = 8 | H = 9 | N = 1

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. lenalidomide and pazinaclone. ::figure[src="https://upload.wikimedia.org/wikipedia/commons/1/11/Lenalidomide_substructures.svg" caption="The drug lenalidomide contains the substructure isoindoline (red)"] ::

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. isoindolines.]] --

Related compounds

References

References

  1. [http://www.chemicalregister.com/Isoindoline/Suppliers/pid63368.htm Isoindoline]
  2. [http://www.chemsynthesis.com/base/chemical-structure-22914.html 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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isoindolines