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Abstract
α-Hydroxyphosphonates 2a-g derived from 2-chloroquinolin-3-carbaldehyde 1a-g by modified Abramov reaction using chloro(trimethyl)silane (TMSCl) and subsequent α-hydroxyphosphonate produced were acetylated using acetic anhydride in the presence of 1,8-Diazabicyclo-undec-7- ene (DBU) to afford the α-acetyloxyphosphonate 3a-g in high yields. The synthesized α- hydroxyphosphonate and α-acetyloxyphosphonate compounds were screened for antibacterial activities. The compound no. 2d, 2e and 3e, 3f has shown comparative activity against their standard Streptomycin.
Highlights
Quinolines[1,2,3] are an important class of heterocyclic compounds
We have studied combination of highly bioactive quinoline compounds with phosphonate for antibacterial activities so as to find new antibacterial bioactive compounds and enrich the quinoline and phosphorus chemistry
The original work of Abramov reaction involved the heating of an aldehyde or a ketone with trialkylphosphite at 70-1000C for several hours in sealed tube[26]
Summary
Quinolines[1,2,3] are an important class of heterocyclic compounds. Several compounds of this class have been screened for biological activities such as bactericidal,[4] antitumor,[5] anti-inflammatory,[6] antimalerial[7] etc. Α-acetyloxyphosphonates are considered as an important and valuable phosphorus compounds for the synthesis of optically active α-hydroxyphosphonates. A search for new biological active compound has stimulated recent studies on the synthesis of α-substituted phosphonates.
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