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Molecules 2016, 21(9), 1140; doi:10.3390/molecules21091140

Practical and Efficient Synthesis of α-Aminophosphonic Acids Containing 1,2,3,4-Tetrahydroquinoline or 1,2,3,4-Tetrahydroisoquinoline Heterocycles

1
Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca 62209, Morelos, Mexico
2
Departamento de Química Orgánica, Universidad de Zaragoza-CSIC, ISQCH, Zaragoza 50009, Spain
*
Authors to whom correspondence should be addressed.
Academic Editor: György Keglevich
Received: 25 July 2016 / Revised: 15 August 2016 / Accepted: 25 August 2016 / Published: 31 August 2016
(This article belongs to the Special Issue Recent Advances in Organophosphorus Chemistry)
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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 δ-lactam with benzyl chloroformate. Finally, the hydrolysis of phosphonate moiety with simultaneous cleavage of the carbamate afforded the target compounds. View Full-Text
Keywords: α-aminophosphonic acids; N-acyliminium ions; conformationally constrained α-aminophosphonic acids; N-acyliminium ions; conformationally constrained
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Ordóñez, M.; Arizpe, A.; Sayago, F.J.; Jiménez, A.I.; Cativiela, C. Practical and Efficient Synthesis of α-Aminophosphonic Acids Containing 1,2,3,4-Tetrahydroquinoline or 1,2,3,4-Tetrahydroisoquinoline Heterocycles. Molecules 2016, 21, 1140.

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