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A new approach towards 1-phenyl and 1-benzyl substituted 2-(aminomethyl)cyclopropanecarboxamides as novel derivatives of the antidepressant Milnacipran

Karel Vervisch UGent, Matthias D'hooghe UGent, Karl Törnroos and Norbert De Kimpe UGent (2009) ORGANIC & BIOMOLECULAR CHEMISTRY. 7(16). p.3271-3279
abstract
2-(2-Cyano-2-phenylethyl)aziridines were converted into novel trans-2-aminomethyl-1-phenylcyclopropanecarboxamides via regiospecific ring opening and 3-exo-tet cyclisation, thus providing the first convenient entry into the trans-isomer of Milnacipran as a useful template for further derivatisation. Furthermore, unprecedented 2-aminomethyl-1-benzylcyclopropanecarboxamides have been synthesized using two different routes starting from 2-( 2- cyanoethyl) aziridines, both involving alpha-benzylation with respect to the nitrile group and aziridine to cyclopropane ring transformation.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
SEROTONIN TRANSPORTER INHIBITORS, NMDA RECEPTOR ANTAGONISTS, POTENT NOREPINEPHRINE, AZIRIDINES, EPOXIDES, ANALOGS, RING, DEPRESSION, MOIETY
journal title
ORGANIC & BIOMOLECULAR CHEMISTRY
Org. Biomol. Chem.
volume
7
issue
16
pages
3271 - 3279
Web of Science type
Article
Web of Science id
000268481500014
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
3.762 (2009)
JCR rank
10/57 (2009)
JCR quartile
1 (2009)
ISSN
1477-0520
DOI
10.1039/b904611a
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
849660
handle
http://hdl.handle.net/1854/LU-849660
date created
2010-02-02 15:32:35
date last changed
2010-02-10 10:16:23
@article{849660,
  abstract     = {2-(2-Cyano-2-phenylethyl)aziridines were converted into novel trans-2-aminomethyl-1-phenylcyclopropanecarboxamides via regiospecific ring opening and 3-exo-tet cyclisation, thus providing the first convenient entry into the trans-isomer of Milnacipran as a useful template for further derivatisation. Furthermore, unprecedented 2-aminomethyl-1-benzylcyclopropanecarboxamides have been synthesized using two different routes starting from 2-( 2- cyanoethyl) aziridines, both involving alpha-benzylation with respect to the nitrile group and aziridine to cyclopropane ring transformation.},
  author       = {Vervisch, Karel and D'hooghe, Matthias and T{\"o}rnroos, Karl and De Kimpe, Norbert},
  issn         = {1477-0520},
  journal      = {ORGANIC \& BIOMOLECULAR CHEMISTRY},
  keyword      = {SEROTONIN TRANSPORTER INHIBITORS,NMDA RECEPTOR ANTAGONISTS,POTENT NOREPINEPHRINE,AZIRIDINES,EPOXIDES,ANALOGS,RING,DEPRESSION,MOIETY},
  language     = {eng},
  number       = {16},
  pages        = {3271--3279},
  title        = {A new approach towards 1-phenyl and 1-benzyl substituted 2-(aminomethyl)cyclopropanecarboxamides as novel derivatives of the antidepressant Milnacipran},
  url          = {http://dx.doi.org/10.1039/b904611a},
  volume       = {7},
  year         = {2009},
}

Chicago
Vervisch, Karel, Matthias D’hooghe, Karl Törnroos, and Norbert De Kimpe. 2009. “A New Approach Towards 1-phenyl and 1-benzyl Substituted 2-(aminomethyl)cyclopropanecarboxamides as Novel Derivatives of the Antidepressant Milnacipran.” Organic & Biomolecular Chemistry 7 (16): 3271–3279.
APA
Vervisch, K., D’hooghe, M., Törnroos, K., & De Kimpe, N. (2009). A new approach towards 1-phenyl and 1-benzyl substituted 2-(aminomethyl)cyclopropanecarboxamides as novel derivatives of the antidepressant Milnacipran. ORGANIC & BIOMOLECULAR CHEMISTRY, 7(16), 3271–3279.
Vancouver
1.
Vervisch K, D’hooghe M, Törnroos K, De Kimpe N. A new approach towards 1-phenyl and 1-benzyl substituted 2-(aminomethyl)cyclopropanecarboxamides as novel derivatives of the antidepressant Milnacipran. ORGANIC & BIOMOLECULAR CHEMISTRY. 2009;7(16):3271–9.
MLA
Vervisch, Karel, Matthias D’hooghe, Karl Törnroos, et al. “A New Approach Towards 1-phenyl and 1-benzyl Substituted 2-(aminomethyl)cyclopropanecarboxamides as Novel Derivatives of the Antidepressant Milnacipran.” ORGANIC & BIOMOLECULAR CHEMISTRY 7.16 (2009): 3271–3279. Print.