practical and efficient synthesis of α-aminophosphonic acids containing 1,2,3,4-tetrahydroquinoline or 1,2,3,4-tetrahydroisoquinoline heterocycles
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ID: 258445
2016
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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.
| Reference Key |
ordez2016moleculespractical
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|---|---|
| Authors | ;Mario Ordóñez;Alicia Arizpe;Fracisco J. Sayago;Ana I. Jiménez;Carlos Cativiela |
| Journal | Journal of ethnopharmacology |
| Year | 2016 |
| DOI |
10.3390/molecules21091140
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| URL | |
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