Münchnone

Münchnone (synonyms: 1,3-oxazolium-5-oxide; 1,3-oxazolium-5-olate; anhydro-5-hydroxy-1,3-oxazolium hydroxide; 5-hydroxy-1,3-oxazolium hydroxide, inner salt; oxido-oxazolium) is a mesoionic heterocyclic aromatic chemical compound.

Munchnone parent compound

Synthesis and reactivity

The first preparation of a münchnone derivative was reported in 1958 by Lawson & Miles by cyclodehydration of 2-pyridone-N-acetic acid with acetic anhydride.[1] The azomethine ylide reactivity of münchnones, and their reaction with alkynes in the synthesis of pyrroles, was first published by Huisgen et al.[2][3] The Huisgen group followed up with a thorough investigation of the chemical properties, reactivity, and utility of münchnones towards the synthesis of many other products.[4][5] As such, they are typically credited for the discovery of the münchnone class of molecules. While certain substituted münchnones are stable and easily isolated under ambient conditions, the majority are unstable, including the parent münchnone itself. Münchnones are typically used as 1,3-dipolar cycloaddition substrates in the synthesis of pyrroles by their in situ generation in the presence of alkynes.

gollark: The weird CC way actually has some benefits.
gollark: That would probably involve a lot of Lua code.
gollark: The closest thing the data cards have is probably SHA-256.
gollark: So just trim that to 16 bytes (and generate a 16 byte IV) and see if it likes that.
gollark: I think you only need 16 bytes of key.

See also

References
  1. Lawson, A.; Miles, D. H. Chem. Ind. (London) 1958, 461.
  2. Huisgen, R.; Gotthardt, H.; Bayer, H. O. Angew. Chem. Int. Ed. Engl. 1964, 3, 135. (doi:10.1002/anie.196401353)
  3. Huisgen, R.; Gotthardt, H.; Bayer, H. O.; Schaefer, F.C. Angew. Chem. Int. Ed. Engl. 1964, 3, 136. (doi:10.1002/anie.196401361)
  4. Gingrich, H. L.; Baum, J. S. In Oxazoles, Chemistry of Heterocyclic Compounds; Turchi, I. J., Ed.; Wiley: New York, 1986; Vol. 45. (doi:10.1002/9780470187289.ch4)
  5. Gribble, G. W. In Oxazoles: Synthesis, Reactions, and Spectroscopy, A; Palmer, D. C., Ed.; Wiley: New York, 2003; Vol. 60. (doi:10.1002/0471428035.ch4)


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.