Practical and efficient synthesis of a-Aminophosphonic acids containing 1, 2, 3, 4-Tetrahydroquinoline or 1, 2, 3, 4-Tetrahydroisoquinoline heterocycles
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: Article (Published version)
Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)

Creative Commons You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.


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 Record created 2016-10-17, last modified 2020-02-21


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