Practical and efficient synthesis of α-Aminophosphonic acids containing 1,2,3,4-Tetrahydroquinoline or 1,2,3,4-Tetrahydroisoquinoline heterocycles

29Citations
Citations of this article
20Readers
Mendeley users who have this article in their library.

Abstract

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 ä-lactam with benzyl chloroformate. Finally, the hydrolysis of phosphonate moiety with simultaneous cleavage of the carbamate afforded the target compounds.

Cite

CITATION STYLE

APA

Ordóñez, M., Arizpe, A., Sayago, F. J., Jiménez, A. I., & Cativiela, C. (2016). Practical and efficient synthesis of α-Aminophosphonic acids containing 1,2,3,4-Tetrahydroquinoline or 1,2,3,4-Tetrahydroisoquinoline heterocycles. Molecules, 21(9). https://doi.org/10.3390/molecules21091140

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free