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Synthesis of a variety of 2-alkyl-2-azabicyclo[3.1.1]heptane-1-carbonitriles via a dynamic addition-intramolecular substitution sequence

Ann De Blieck UGent and Chris Stevens UGent (2011) SYNLETT. p.1748-1752
abstract
An improved two-step synthetic approach towards 3-(2-chloroethyl) cyclobutanone is described and used in the synthesis of a class of 2-alkyl-2-azabicyclo[3.1.1]heptane-1-carbonitriles. The key step consists of a reversible addition of hydrogen cyanide onto the in situ generated imines, followed by an intramolecular nucleophilic substitution, thereby leading to the bicyclic skeleton in moderate to good yields (47-92%). These bicyclic compounds are stable, and the incorporated cyano group can be easily reduced to the corresponding aminomethyl group in high yields (93-99%), using lithium aluminum hydride.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
ring closure, nucleophilic addition, bicyclic compounds, heterocycles, nitriles, 2, 4-METHANOPROLINE 2-CARBOXY-2, 4-METHANOPYRROLIDINE, CONFORMATIONAL PROPERTIES, VINYLOGOUS IMIDE, AQUEOUS-SOLUTION, HERBERT-SMITHII, AMINO-ACIDS, DERIVATIVES, PEPTIDES, H-1-NMR, ANALOGS
journal title
SYNLETT
Synlett
issue
12
pages
1748 - 1752
Web of Science type
Article
Web of Science id
000292596600023
JCR category
CHEMISTRY, ORGANIC
JCR impact factor
2.71 (2011)
JCR rank
18/56 (2011)
JCR quartile
2 (2011)
ISSN
0936-5214
DOI
10.1055/s-0030-1260811
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
1997160
handle
http://hdl.handle.net/1854/LU-1997160
date created
2012-01-19 15:50:44
date last changed
2012-02-09 15:20:19
@article{1997160,
  abstract     = {An improved two-step synthetic approach towards 3-(2-chloroethyl) cyclobutanone is described and used in the synthesis of a class of 2-alkyl-2-azabicyclo[3.1.1]heptane-1-carbonitriles. The key step consists of a reversible addition of hydrogen cyanide onto the in situ generated imines, followed by an intramolecular nucleophilic substitution, thereby leading to the bicyclic skeleton in moderate to good yields (47-92\%). These bicyclic compounds are stable, and the incorporated cyano group can be easily reduced to the corresponding aminomethyl group in high yields (93-99\%), using lithium aluminum hydride.},
  author       = {De Blieck, Ann and Stevens, Chris},
  issn         = {0936-5214},
  journal      = {SYNLETT},
  keyword      = {ring closure,nucleophilic addition,bicyclic compounds,heterocycles,nitriles,2,4-METHANOPROLINE 2-CARBOXY-2,4-METHANOPYRROLIDINE,CONFORMATIONAL PROPERTIES,VINYLOGOUS IMIDE,AQUEOUS-SOLUTION,HERBERT-SMITHII,AMINO-ACIDS,DERIVATIVES,PEPTIDES,H-1-NMR,ANALOGS},
  language     = {eng},
  number       = {12},
  pages        = {1748--1752},
  title        = {Synthesis of a variety of 2-alkyl-2-azabicyclo[3.1.1]heptane-1-carbonitriles via a dynamic addition-intramolecular substitution sequence},
  url          = {http://dx.doi.org/10.1055/s-0030-1260811},
  year         = {2011},
}

Chicago
De Blieck, Ann, and Chris Stevens. 2011. “Synthesis of a Variety of 2-alkyl-2-azabicyclo[3.1.1]heptane-1-carbonitriles via a Dynamic Addition-intramolecular Substitution Sequence.” Synlett (12): 1748–1752.
APA
De Blieck, A., & Stevens, C. (2011). Synthesis of a variety of 2-alkyl-2-azabicyclo[3.1.1]heptane-1-carbonitriles via a dynamic addition-intramolecular substitution sequence. SYNLETT, (12), 1748–1752.
Vancouver
1.
De Blieck A, Stevens C. Synthesis of a variety of 2-alkyl-2-azabicyclo[3.1.1]heptane-1-carbonitriles via a dynamic addition-intramolecular substitution sequence. SYNLETT. 2011;(12):1748–52.
MLA
De Blieck, Ann, and Chris Stevens. “Synthesis of a Variety of 2-alkyl-2-azabicyclo[3.1.1]heptane-1-carbonitriles via a Dynamic Addition-intramolecular Substitution Sequence.” SYNLETT 12 (2011): 1748–1752. Print.