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Synthesis of 2-hydroxy-1,4-oxazin-3-ones through ring transformation of 3-hydroxy-4-(1,2-dihydroxyethyl)-β-lactams and a study of their reactivity

Karen Mollet, Hannelore Goossens UGent, Nicola Piens, Saron Catak UGent, Michel Waroquier UGent, Karl W Tornroos, Veronique Van Speybroeck UGent, Matthias D'hooghe UGent and Norbert De Kimpe UGent (2013) CHEMISTRY-A EUROPEAN JOURNAL. 19(10). p.3383-3396
abstract
The reactivity of 3-hydroxy-4-(1,2-dihydroxyethyl)--lactams with regard to the oxidant sodium periodate was evaluated, unexpectedly resulting in the exclusive formation of new 2-hydroxy-1,4-oxazin-3-ones through a C3C4 bond cleavage of the intermediate 4-formyl-3-hydroxy--lactams followed by a ring expansion. This peculiar transformation stands in sharp contrast with the known NaIO4-mediated oxidation of 3-alkoxy- and 3-phenoxy-4-(1,2-dihydroxyethyl)--lactams, which exclusively leads to the corresponding 4-formyl--lactams without a subsequent ring enlargement. In addition, this new class of functionalized oxazin-3-ones was further evaluated for its potential use as building blocks in the synthesis of a variety of differently substituted oxazin-3-ones, morpholin-3-ones and pyrazinones. Furthermore, additional insights into the mechanism and the factors governing this new ring-expansion reaction were provided by means of density functional theory calculations.
Please use this url to cite or link to this publication:
author
organization
alternative title
Synthesis of 2-hydroxy-1,4-oxazin-3-ones through ring transformation of 3-hydroxy-4-(1,2-dihydroxyethyl)--lactams and a study of their reactivity
year
type
journalArticle (original)
publication status
published
subject
keyword
bond cleavage, beta-lactams, density functional calculations, oxazin-3-ones, reaction mechanisms, ring expansion, CARBONIUM ION REARRANGEMENTS, TRICYCLIC BETA-LACTAMS, BUILDING-BLOCKS, STEREOCONTROLLED SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, ASYMMETRIC-SYNTHESIS, MEDICINAL CHEMISTRY, SYNTHON METHOD, DERIVATIVES, MOLECULES
journal title
CHEMISTRY-A EUROPEAN JOURNAL
Chem.-Eur. J.
volume
19
issue
10
pages
3383 - 3396
Web of Science type
Article
Web of Science id
000315399700019
JCR category
CHEMISTRY, MULTIDISCIPLINARY
JCR impact factor
5.696 (2013)
JCR rank
22/148 (2013)
JCR quartile
1 (2013)
ISSN
0947-6539
DOI
10.1002/chem.201203314
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
3177783
handle
http://hdl.handle.net/1854/LU-3177783
date created
2013-03-28 11:02:51
date last changed
2016-12-19 15:47:00
@article{3177783,
  abstract     = {The reactivity of 3-hydroxy-4-(1,2-dihydroxyethyl)--lactams with regard to the oxidant sodium periodate was evaluated, unexpectedly resulting in the exclusive formation of new 2-hydroxy-1,4-oxazin-3-ones through a C3C4 bond cleavage of the intermediate 4-formyl-3-hydroxy--lactams followed by a ring expansion. This peculiar transformation stands in sharp contrast with the known NaIO4-mediated oxidation of 3-alkoxy- and 3-phenoxy-4-(1,2-dihydroxyethyl)--lactams, which exclusively leads to the corresponding 4-formyl--lactams without a subsequent ring enlargement. In addition, this new class of functionalized oxazin-3-ones was further evaluated for its potential use as building blocks in the synthesis of a variety of differently substituted oxazin-3-ones, morpholin-3-ones and pyrazinones. Furthermore, additional insights into the mechanism and the factors governing this new ring-expansion reaction were provided by means of density functional theory calculations.},
  author       = {Mollet, Karen and Goossens, Hannelore and Piens, Nicola and Catak, Saron and Waroquier, Michel and Tornroos, Karl W and Van Speybroeck, Veronique and D'hooghe, Matthias and De Kimpe, Norbert},
  issn         = {0947-6539},
  journal      = {CHEMISTRY-A EUROPEAN JOURNAL},
  keyword      = {bond cleavage,beta-lactams,density functional calculations,oxazin-3-ones,reaction mechanisms,ring expansion,CARBONIUM ION REARRANGEMENTS,TRICYCLIC BETA-LACTAMS,BUILDING-BLOCKS,STEREOCONTROLLED SYNTHESIS,STEREOSELECTIVE-SYNTHESIS,ASYMMETRIC-SYNTHESIS,MEDICINAL CHEMISTRY,SYNTHON METHOD,DERIVATIVES,MOLECULES},
  language     = {eng},
  number       = {10},
  pages        = {3383--3396},
  title        = {Synthesis of 2-hydroxy-1,4-oxazin-3-ones through ring transformation of 3-hydroxy-4-(1,2-dihydroxyethyl)-\ensuremath{\beta}-lactams and a study of their reactivity},
  url          = {http://dx.doi.org/10.1002/chem.201203314},
  volume       = {19},
  year         = {2013},
}

Chicago
Mollet, Karen, Hannelore Goossens, Nicola Piens, Saron Catak, Michel Waroquier, Karl W Tornroos, Veronique Van Speybroeck, Matthias D’hooghe, and Norbert De Kimpe. 2013. “Synthesis of 2-hydroxy-1,4-oxazin-3-ones Through Ring Transformation of 3-hydroxy-4-(1,2-dihydroxyethyl)-β-lactams and a Study of Their Reactivity.” Chemistry-a European Journal 19 (10): 3383–3396.
APA
Mollet, K., Goossens, H., Piens, N., Catak, S., Waroquier, M., Tornroos, K. W., Van Speybroeck, V., et al. (2013). Synthesis of 2-hydroxy-1,4-oxazin-3-ones through ring transformation of 3-hydroxy-4-(1,2-dihydroxyethyl)-β-lactams and a study of their reactivity. CHEMISTRY-A EUROPEAN JOURNAL, 19(10), 3383–3396.
Vancouver
1.
Mollet K, Goossens H, Piens N, Catak S, Waroquier M, Tornroos KW, et al. Synthesis of 2-hydroxy-1,4-oxazin-3-ones through ring transformation of 3-hydroxy-4-(1,2-dihydroxyethyl)-β-lactams and a study of their reactivity. CHEMISTRY-A EUROPEAN JOURNAL. 2013;19(10):3383–96.
MLA
Mollet, Karen, Hannelore Goossens, Nicola Piens, et al. “Synthesis of 2-hydroxy-1,4-oxazin-3-ones Through Ring Transformation of 3-hydroxy-4-(1,2-dihydroxyethyl)-β-lactams and a Study of Their Reactivity.” CHEMISTRY-A EUROPEAN JOURNAL 19.10 (2013): 3383–3396. Print.