Surf Wiki
Save to docs
general/isoindoles

From Surf Wiki (app.surf) — the open knowledge base

Isoindole

In organic chemistry and heterocyclic chemistry, isoindole consists of a benzene ring fused with pyrrole. The compound is an isomer of indole. Its reduced form is isoindoline. The parent isoindole is a rarely encountered in the technical literature, but substituted derivatives are useful commercially and occur naturally. Isoindoles units occur in phthalocyanines, an important family of dyes. Some alkaloids containing isoindole have been isolated and characterized.See for example: {{Cite journal

Synthesis

The parent isoindole was prepared by flash vacuum pyrolysis of an N-substituted isoindoline. N-Substituted isoindoles, which are easier to handle, can be prepared by dehydration of isoindoline-N-oxides. They also arise by myriad other methods, e.g., starting from xylylene dibromide (C6H4(CH2Br)2).

Structure and tautomerism of 2-H-isoindoles

Unlike indole, isoindoles exhibit noticeable alternation in the C-C bond lengths, which is consistent with their description as pyrrole derivatives fused to a butadiene.

In solution, the 2H-isoindole tautomer predominates. It resembles a pyrrole more than a simple imine. The degree to which the 2H predominates depends on the solvent, and can vary with the substituent in substituted isoindoles.

:[[File:Isoindoletautomerism.svg|class=skin-invert-image|thumb|left|400px|2H-Isoindole (right) is the predominant tautomer relative to 1H-isoindole (left)]]

N-Substituted isoindoles do not engage is tautomerism and are therefore simpler to study.

References

References

  1. [[International Union of Pure and Applied Chemistry]]. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". [[Royal Society of Chemistry.
  2. Gilchrist, T. L.. (1987). "Heterocyclic Chemistry". Longman.
  3. Heugebaert, Thomas S. A.; Roman, Bart I.; Stevens, Christian V. "Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles" Chemical Society Reviews 2012, volume 41, pp. 5626-5640. {{doi. 10.1039/c2cs35093a
  4. R. Bonnett and R. F. C. Brown "Isoindole" J. Chem. Soc., Chem. Commun., 1972, 393-395. {{doi. 10.1039/C39720000393
  5. (2010). "Handbook of Heterocyclic Chemistry". Elsevier.
  6. (2010). "Heterocyclic Chemistry". John Wiley & Sons.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

isoindoles simple-aromatic-rings
Want to explore this topic further?

Ask Mako anything about Isoindole — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report