Cleavage of Diethyl Chromonyl alpha-Aminophosponate with Nitrogen and Carbon Nucleophiles: A Synthetic Approach and Biological Evaluations of a Series of Novel Azoles, Azines, and Azepines Containing alpha-Aminophosphonate and Phosphonate Groups
Ali, TE; Abdel-Aziz, SA; El-Edfawy, SM; Abdel-Kariem, S. M.; Mohamed, E.A.;
Abstract
A convenient synthetic approach leading to a series of novel substituted azoles, azines, and azepines linked to the α-aminophosphonate moiety was achieved. The methodology depends on ring opening and ring closure (RORC) of the chromone ring of diethyl chromonyl α-aminophosphonate 1 via its reaction with nitrogen nucleophiles such as primary amines and 1,2-, 1,3-, and 1,4-bi-nucleophiles in ethanolic sodium ethoxide. Also, treatment of compound 1 with some acyclic and cyclic active methylene compounds under the same reaction conditions afforded interesting novel isolated and fused pyridine systems bearing phosphonate groups at the α-position. The screening of antimicrobial activity for the synthesized compounds indicates that connection of pyrazole, oxazepine, and benzodiazepine rings with α-aminophosphonate moiety exhibited good antimicrobial effects. Also, evaluation of their antioxidant properties shows that the compounds having 1,5-benzoxazepinyl and 1,5-benzodiazepinyl units in combination with α-aminophosphonic diester moiety are the most powerful antioxidant agents.
Other data
Title | Cleavage of Diethyl Chromonyl alpha-Aminophosponate with Nitrogen and Carbon Nucleophiles: A Synthetic Approach and Biological Evaluations of a Series of Novel Azoles, Azines, and Azepines Containing alpha-Aminophosphonate and Phosphonate Groups | Authors | Ali, TE; Abdel-Aziz, SA; El-Edfawy, SM; Abdel-Kariem, S. M. ; Mohamed, E.A. | Keywords | ESTERS;antioxidant;phosphonate;antimicrobial;chromone;alpha-Aminophosphonate;CRYSTAL-STRUCTURE;DERIVATIVES;INHIBITORS;COMPLEXES;CHEMISTRY;CATALYST;ACIDS;ANALOGS;OXIDES | Issue Date | 2014 | Publisher | TAYLOR & FRANCIS INC | Journal | Synthetic Communications | ISSN | 0039-7911 | DOI | 10.1080/00397911.2014.948965 | Scopus ID | 2-s2.0-84922079601 | Web of science ID | WOS:000343284500010 |
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