Resumen: We report here a practical and efficient synthesis of a-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. Idioma: Inglés DOI: 10.3390/molecules21091140 Año: 2016 Publicado en: Molecules 21, 9 (2016), [14 pp] ISSN: 1420-3049 Factor impacto JCR: 2.861 (2016) Categ. JCR: CHEMISTRY, ORGANIC rank: 17 / 59 = 0.288 (2016) - Q2 - T1 Factor impacto SCIMAGO: 0.824 - Analytical Chemistry (Q1) - Pharmaceutical Science (Q1) - Chemistry (miscellaneous) (Q1) - Organic Chemistry (Q2) - Physical and Theoretical Chemistry (Q2) - Drug Discovery (Q2) - Medicine (miscellaneous) (Q2) - Molecular Medicine (Q3)