General procedure for the synthesis of 1-acetoxy-1H-indene-2-carboxylic acid alkyl ester 2a-eTo a mixture of alcohol 1 (5 mmoles), acetic anhydride (25 mmoles) in 40 mL of anhydrous ether cooled at 0 °C under stirring in nitrogen atmosphere, was added a drop of concentrated sulfuric acid. After completion of the reaction, the mixture was hydrolyzed with ice water and extracted with ether (3x20 mL). The organic layers were washed successively with sodium hydroxide solution (1.5M) and brine until neutral pH then dried over MgSO 4 and concentrated in vacuo. After evaporating of the solvent, The residue obtained was purified by silica gel column chromatography (AcOEt:Hexane, 7/3). The spectral ( 1 H and 13 C NMR and HRMS) data of the unknown compounds 2a-e are given below.Selected Data 1-Acetoxy-1H-indene-2-carboxylic acid methyl ester 2a
A simple, convenient and highly stereoselective synthesis of diethyl (E)-1-(bromomethyl)-2-cyanovinylphosphonate 4 is described. The product would be a useful substrate for the synthesis of diethyl 1-[(alkylamino)(cyano)methyl]vinylphosphonates 5 via allylic rearrangement S N 2 -type mechanism.
Selected Reactions of Diethyl (E)-1-(Bromomethyl)-2-cyanovinylphosphonate with Secondary and Tertiary Amines. -The reaction of phosphonate (I) with less bulky secondary amines leads to phosphonates of type (III)/(IV) after substitution and rearrangement. More bulky secondary amines afford the normal substitution products of type (V). The reaction with tertiary amines affords phosphonate (VII). -(FRAY, A.; BEN KRAIEM, J.; AMRI*, H.; Heteroat. Chem. 24 (2013) 6, 460-465, http://dx.doi.org/10.1002/hc.21112 ; Fac. Sci. Tunis, Univ. El-Manar, 2092 El Manar, Tunis, Tunisia; Eng.) -M. Bohle 15-205
New and highly functionalized 1,3-dienes 3 and 4 have been synthesized via two different pathways starting from allyl bromide 1. Firstly, the reaction of allyl bromide 1 with triethylphosphite leads to an allylphosphonate 2, which undergoes the Wittig-Horner reaction with a range of saturated and unsaturated aldehydes gives rise to the corresponding 1,3-dienes 3. Secondly, a highly stereoselective reaction between allyl bromide 1 and nitroalkane salts, offers the possibility to obtaining functionalized (E)-1,3-dienes 4.
 This paper describes a convenient synthesis of novel series of 3,4-disubstituted pyrrolidines based on the aza-Michael addition of primary amines to 3,4-difunctionalized-1,3-diene followed by an intramolecular cyclization.
An elegant one-pot synthesis of new indenols 2 was successfully carried out, starting from 1-hydroxy-1H-indene-2-carboxylic acid 1. Thus, esterification of acid 1 with aliphatic alcohols in toluene at reflux and a catalytic amount of para-toluenesulfonic acid afforded the corresponding alkyl esters 2 in moderate to good yields. This classical esterification process enables an efficient entry to a variety of new indenol-based molecular models 2, which could be adapted to a range of drug candidates. All the synthesized compounds 2a-e were subjected to the preliminary evaluation for their potential anti-oxidant and anti-bacterial activities. The assessment of radical scavenging capacity of the compounds 2a-e towards the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) was measured and these compounds were found to scavenge DPPH free radical efficiently. Moreover, the in vitro antibacterial activity of derivatives 2a-e has been tested against a panel of pathogenic agents to show potent activity against all sensitive and resistant ones.
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