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, with the molecular formula C3H3NO2. The name refers to the city of Munich, Germany (German: München), where the compound and its derivatives were first discovered and studied.[1]
 Munchnone parent compound
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| IUPAC name
1,3-oxazol-5-ol
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C3H3NO2 | |
| Molar mass | 85.062 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactivity
editThe first preparation of a münchnone derivative was reported in 1959 by Lawson & Miles by cyclodehydration of 2-pyridone-N-acetic acid with acetic anhydride.[2] The azomethine ylide reactivity of münchnones, and their reaction with alkynes in the synthesis of pyrroles, was first published by Huisgen et al.[3][4] 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.[5][6] 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.[1]
See also
editReferences
edit- ^ a b Reissig, Hans-Ulrich; Zimmer, Reinhold (2014-09-08). "Münchnones-New Facets after 50 Years". Angewandte Chemie International Edition. 53 (37): 9708–9710. doi:10.1002/anie.201405092. PMID 25045012.
- ^ Lawson, Alexander; Miles, D. H. (1 January 1959). "574. Some new mesoionic compounds". Journal of the Chemical Society (Resumed): 2865–2871. doi:10.1039/JR9590002865.
- ^ Huisgen, R.; Gotthardt, H.; Bayer, H. O. (February 1964). "Azlactones as 1,3‐Dipoles; A New Pyrrole Synthesis". Angewandte Chemie International Edition in English. 3 (2): 135–136. doi:10.1002/anie.196401353. ISSN 0570-0833.
- ^ Huisgen, R.; Gotthardt, H.; Bayer, H. O.; Schaefer, F. C. (February 1964). "A New Type of Mesoionic Aromatic Compound and Its 1,3‐Dipolar Cycloaddition Reactions with Acetylene Derivatives". Angewandte Chemie International Edition in English. 3 (2): 136–137. doi:10.1002/anie.196401361. ISSN 0570-0833.
- ^ Gingrich, Henry L.; Baum, Jonathan S. (January 1986). Turchi, I. J. (ed.). Mesoionic Oxazoles. Vol. 45 (1 ed.). Wiley. pp. 731–961. doi:10.1002/9780470187289.ch4. ISBN 978-0-471-86958-0.
- ^ Gribble, Gordon W. (2003-07-25). Palmer, David C. (ed.). Mesoionic Oxazoles. Vol. 60. Hoboken, NJ, USA: John Wiley & Sons, Inc. pp. 473–576. doi:10.1002/0471428035.ch4. ISBN 978-0-471-39494-5.