Next Article in Journal
Purification of Flavonoids from Chinese Bayberry (Morella rubra Sieb. et Zucc.) Fruit Extracts and α-Glucosidase Inhibitory Activities of Different Fractionations
Next Article in Special Issue
Palladium-Catalyzed Allylation/Benzylation of H-Phosphinate Esters with Alcohols
Previous Article in Journal
Panax Notoginseng Saponins as a Novel Nature Stabilizer for Poorly Soluble Drug Nanocrystals: A Case Study with Baicalein
Previous Article in Special Issue
Stereoselective Synthesis of α-Amino-C-phosphinic Acids and Derivatives
Article Menu
Issue 9 (September) cover image

Export Article

Open AccessArticle
Molecules 2016, 21(9), 1140;

Practical and Efficient Synthesis of α-Aminophosphonic Acids Containing 1,2,3,4-Tetrahydroquinoline or 1,2,3,4-Tetrahydroisoquinoline Heterocycles

Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca 62209, Morelos, Mexico
Departamento de Química Orgánica, Universidad de Zaragoza-CSIC, ISQCH, Zaragoza 50009, Spain
Authors to whom correspondence should be addressed.
Academic Editor: György Keglevich
Received: 25 July 2016 / Revised: 15 August 2016 / Accepted: 25 August 2016 / Published: 31 August 2016
(This article belongs to the Special Issue Recent Advances in Organophosphorus Chemistry)
Full-Text   |   PDF [1279 KB, uploaded 31 August 2016]   |  


We report here a practical and efficient synthesis of α-aminophosphonic acid incorporated into 1,2,3,4-tetrahydroquinoline and 1,2,3,4-tetrahydroisoquinoline heterocycles, which could be considered to be conformationally constrained analogues of pipecolic acid. The principal contribution of this synthesis is the introduction of the phosphonate group in the N-acyliminium ion intermediates, obtained from activation of the quinoline and isoquinoline heterocycles or from the appropriate δ-lactam with benzyl chloroformate. Finally, the hydrolysis of phosphonate moiety with simultaneous cleavage of the carbamate afforded the target compounds. View Full-Text
Keywords: α-aminophosphonic acids; N-acyliminium ions; conformationally constrained α-aminophosphonic acids; N-acyliminium ions; conformationally constrained

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

Supplementary materials

  • Supplementary File 1:

    Supplementary (PDF, 984 KB)

  • Externally hosted supplementary file 1
    Link: http://no
    Description: NMR data

Share & Cite This Article

MDPI and ACS Style

Ordóñez, M.; Arizpe, A.; Sayago, F.J.; Jiménez, A.I.; Cativiela, C. Practical and Efficient Synthesis of α-Aminophosphonic Acids Containing 1,2,3,4-Tetrahydroquinoline or 1,2,3,4-Tetrahydroisoquinoline Heterocycles. Molecules 2016, 21, 1140.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top