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- Title
Practical and Efficient Synthesis of α-Aminophosphonic Acids Containing 1,2,3,4-Tetrahydroquinoline or 1,2,3,4-Tetrahydroisoquinoline Heterocycles.
- Authors
Ordóñez, Mario; Arizpe, Alicia; Sayago, Fracisco J.; Jiménez, Ana I.; Cativiela, Carlos
- Abstract
We report here a practical and efficient synthesis of -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.
- Subjects
TETRAHYDROISOQUINOLINES; HETEROCYCLIC compounds; PIPECOLIC acid; QUINOLINE; ISOQUINOLINE
- Publication
Molecules, 2016, Vol 21, Issue 9, p1140
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules21091140