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

Ordóñez, M. ; Arizpe, A. ; Sayago, F.J. (Universidad de Zaragoza) ; Jiménez, A.I. (Universidad de Zaragoza) ; Cativiela, C. (Universidad de Zaragoza)

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)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E40
Financiación: info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2013-40855-R

Tipo y forma: Artículo (Versión definitiva)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)