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.
CITATION STYLE
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
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