Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 3
329
Views
3
CrossRef citations to date
0
Altmetric
Articles

An improved synthesis of 4-aminobutanenitrile from 4-azidobutanenitrile and comments on room temperature stability

ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon
Pages 428-436 | Received 02 Sep 2020, Published online: 17 Dec 2020

References

  • Fleming, F. F.; Yao, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C. Nitrile-Containing Pharmaceuticals: Efficacious Roles of the Nitrile Pharmacophore. J. Med. Chem. 2010, 53, 7902–7917. DOI: 10.1021/jm100762r.
  • Yuan, H.; Silverman, R. B. New Substrates and Inhibitors of Gamma-Aminobutyric Acid Aminotransferase Containing Bioisosteres of the Carboxylic Acid Group: Design, Synthesis, and Biological Activity. Bioorg. Med. Chem. 2006, 14, 1331–1338. DOI: 10.1016/j.bmc.2005.09.067.
  • Hoffer, B. W.; Schoenmakers, P. H. J.; Mooijman, P. R. M.; Hamminga, G. M.; Berger, R. J.; van Langeveld, A. D.; Moulijn, J. A. Mass Transfer and Kinetics of the Three-Phase Hydrogenation of a Dinitrile over a Raney-Type Nickel Catalyst. Chem. Eng. Sci. 2004, 59, 259–269. DOI: 10.1016/S0009-2509(03)00303-8.
  • Serra, M.; Salagre, P.; Cesteros, Y.; Medina, F.; Sueiras, J. E. Nickel and Nickel–Magnesia Catalysts Active in the Hydrogenation of 1,4-Butanedinitrile. J. Catal. 2001, 197, 210–219. DOI: 10.1006/jcat.2000.3084.
  • Reissner, T.; Altenhoff, A. G.; Mueller, C.; Fischer, R.-H. Method for the Preparation of Polyamines from Dinitriles and/or Amino Nitriles. U.S. Patent 20190218341, July 18, 2019.
  • Lin-Vien, D.; Colthup, N. B.; Fateley, W. G.; Grasselli, J. G. Chapter 8. The –C≡N and –N≡C Groups. In The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules; Lin-Vien, D., Colthup, N. B., Fateley, W. G., Grasselli, J. G., Eds.; Academic Press: San Diego, CA, 1991; pp 105–115. DOI: 10.1016/B978-0-08-057116-4.50014-6.
  • Deb, P.; Haldar, T.; Kashid, S. M.; Banerjee, S.; Chakrabarty, S.; Bagchi, S. Correlating Nitrile IR Frequencies to Local Electrostatics Quantifies Noncovalent Interactions of Peptides and Proteins. J. Phys. Chem. B. 2016, 120, 4034–4046. DOI: 10.1021/acs.jpcb.6b02732.
  • Fringuelli, F.; Pizzo, F.; Vaccaro, L. Cobalt(II) Chloride-Catalyzed Chemoselective Sodium Borohydride Reduction of Azides in Water. Synthesis 2000, 2000, 646–650. DOI: 10.1055/s-2000-6389.
  • Staudinger, H.; Meyer, J. Über Neue Organische Phosphorverbindungen III. Phosphinmethylenderivate Und Phosphinimine. Helvetica 1919, 2, 635–646. DOI: 10.1002/hlca.19190020164.
  • Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Sixty Years of Staudinger Reaction. Tetrahedron 1981, 37, 437–472. DOI: 10.1016/S0040-4020(01)92417-2.
  • Gololobov, Y. G.; Kasukhin, L. F. Recent Advances in the Staudinger Reaction. Tetrahedron 1992, 48, 1353–1406. DOI: 10.1016/S0040-4020(01)92229-X.
  • Pauli, G. F.; Chen, S.-N.; Simmler, C.; Lankin, D. C.; Gödecke, T.; Jaki, B. U.; Friesen, J. B.; McAlpine, J. B.; Napolitano, J. G. Importance of Purity Evaluation and the Potential of Quantitative 1H NMR as a Purity Assay. J. Med. Chem. 2014, 57, 9220–9231. DOI: 10.1021/jm500734a.
  • Gratchev, M. K.; Kurochkina, G. I.; Negrebetsky, V. V.; Nifantyev, E. E. The Synthesis and Structure of P(Iii)-Phosphorylated 2-Aminopyrrolines. Phosphorus Sulfur Silicon Relat. Elem. 1994, 88, 257–269. DOI: 10.1080/10426509408036930.
  • Laval, S.; Dayoub, W.; Pehlivan, L.; Métay, E.; Favre-Reguillon, A.; Delbrayelle, D.; Mignani, G.; Lemaire, M. Straightforward Access to Cyclic Amines by Dinitriles Reduction. Tetrahedron 2014, 70, 975–983. DOI: 10.1016/j.tet.2013.11.101.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.