Abstract
A highly convenient method has been developed for the synthesis of (prop-2-ynyloxy) benzene and its derivatives. Differently substituted phenol and aniline derivatives were allowed to react with propargyl bromide in the presence of K2CO3 base and acetone as solvent. The compounds were synthesized in good yields (53–85%). Low cost, high yields and easy availability of compounds helped in the synthesis. Electron withdrawing groups favor the formation of stable phenoxide ion thus in turn favors the formation of product while electron donating groups do not favor the reaction. Phenol derivatives gave good yields as compared to that of aniline. As aprotic polar solvents favor SN2 type reactions so acetone provided best solvation for the reactions. K2CO3 was proved to be good for the synthesis. Antibacterial, Antiurease and NO scavenging activity of synthesized compounds were also examined. 4-bromo-2-chloro-1-(prop-2-ynyloxy)benzene 2a was found most active compound against urease enzyme with a percentage inhibition of 82.00±0.09 at 100 µg/mL with IC50 value of 60.2. 2-bromo-4-methyl-1-(prop-2-ynyloxy)benzene 2d was found potent antibacterial against Bacillus subtillus showing excellent inhibitory action with percentage inhibition of 55.67±0.26 at 100 µg/ml wih IC50 value of 79.9. Based on results, it can be concluded that some of the synthesized compounds may have potential antiurease and antibacterial effects against several harmful substances.
Highlights
Terminal alkynes provide an efficient method for the synthesis of triazole, [21] which can be prepared by reaction of 3-Bromopropyne and aniline derivatives in DMF [9, 22]
We reported the reaction of phenol and propargyl bromide for the synthesis of (Prop-2-ynyloxy)benzene derivatives under different reaction conditions. [23,24,25,26,27,28] There is very little work on the synthesis of reported compounds under these optimized reaction conditions and so far no information was published for antibacterial, antiurease and Nitric oxide (NO) scavenging activity of the synthesized compounds
When compound was first stirred in the presence of K2CO3 (3.5 eq.) and acetone at room temperature for 2 hour adding propargyl bromide (1.3 eq.) to the reaction mixture and stirring for 16 hour resulted in 53% yield
Summary
(Prop-2-ynyloxy)benzene is an important compound having vast synthetic applications. Most important of all of its applications is its use as triazole intermediate [1]. [4] The main intention of the present work is the synthesis of (Prop-2-ynyloxy)benzene derivatives by reported methodologies [12,13,14,15,16,17,18,19,20] and our focused to adopt optimization reaction condition such as effect of solvents, moler concentration of bases, stirring and refluxing time. In addition evaluating their antibacterial, antiurease and NO scavenging activities
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