Indolizine

Last updated
Indolizine
Indolizin - Indolizine.svg
Indolizine ball-and-stick.png
Names
Preferred IUPAC name
Indolizine [1]
Other names
Pyrrocoline; Indolizin; Pyrrolo[1,2-a]pyridine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.219.195 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H7N/c1-2-6-9-7-3-5-8(9)4-1/h1-7H Yes check.svgY
    Key: HOBCFUWDNJPFHB-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C8H7N/c1-2-6-9-7-3-5-8(9)4-1/h1-7H
    Key: HOBCFUWDNJPFHB-UHFFFAOYAH
  • c1ccc2ccccn12
Properties
C8H7N
Molar mass 117.151 g·mol−1
AppearanceWhite solid
Melting point 75 °C (167 °F; 348 K)
Boiling point 205 °C (401 °F; 478 K)
Basicity (pKb)10.1 [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Indolizine is an heterocyclic compound with the formula C8H7N). It is an uncommon isomer of indole with the nitrogen located at a ring fusion position. The saturated analog is indolizidine, which is the core of a variety of alkaloids such as swainsonine. [3]

Examples of some simple fully synthetic substituted indolizines include 2ZEDMA, 1ZP2MA, and 1Z2MAP1O. [4] [5]

References

  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 213. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. Elattar, K.M.; Youssef, I.; Fadda, A.A. (4 May 2016). "Reactivity of indolizines in organic synthesis". Synthetic Communications Reviews. 46 (9): 719–744. doi:10.1080/00397911.2016.1166252. S2CID   100777050.
  3. Julio Alvarez-Builla; Juan Jose Vaquero; José Barluenga, eds. (2011). Modern Heterocyclic Chemistry. Wiley-VCH.
  4. WOapplication 2023081306A1, Baggott MJ,"Indolizine compounds for the treatment of mental disorders or mental enhancement",published 11 May 2023, assigned to Tactogen
  5. WOpatent 2023183613A2, Baggott MJ,"Indolizine compounds for the treatment of mental disorders or inflammation",published 2023 September 28, assigned to Tactogen