- Reaction 1: Acrylic acid 200mg (190$\mu $ l) (1 eq) was taken in a r.b and dissolved in required amount of DCM. 860mg of DCC (1.5 eq) was added to the reaction mixture to form white ppt and stirred for 15 minutes. Then 330mg of 8-hydroxyquinoline (0.8eq) was added to the white solution and stirred at r.t for 2 hr. Solution color changes to brown. After completion of 2 hr, DCU was separated by filtration and filtrate was washed with water. Organic layer was collected and dried over anhydrous sodium sulphate. Organic layer (DCM) was evaporated to get product.
- Reaction 2: 200mg (190$\mu $l) of Acrylic acid (1 eq) was taken in a r.b and dissolved in required amount of methanol. 860mg of DCC (1.5 eq) was added to the reaction mixture to form white ppt and stirred for 15 minutes. Then 206mg i.e 202$\mu $l of aniline (0.8eq) was added to the white solution and stirred at r.t for 2 hr. After completion of 2 hr, DCU was separated by filtration and filtrate was washed with water. Organic layer was collected and dried over anhydrous sodium sulphate. Organic layer was evaporated to get product.
- Reaction 3: 200mg of benzoic acid (1equivalent) was dissolved in DMF, then to it 1.2 eqnt of DCC i.e 405mg was added and stirred for 15 min. To this solution 240mg of DMAP (1.2 equivalent) was added. The reaction mixture allowed to stir for 30 min at room temperature. 152mg of Aniline (1equivalent) i.e 148$\mu $l was dissolved in dimethyl formamide and this solution was added to the reaction mixture at 0-5C. Reaction mixture was stirred for another 30 minutes at 0-5C. Charged ethyl acetate followed by water to the reaction mixture. Organic layer was washed with 2 x 10 ml of water followed by sodium bicarbonate wash. Finally organic layer was washed with brine solution. Organic layer concentrated under vacuum to yield product.
- Reaction 4: A 25-mL, round-bottom flask was charged with the specified amount of N-hydroxysuccinimide (3.53 g, 30.7 mmol, 1 eq) and triethylamine (4.7 g, 33.7 mmol, 1.1 eq) in 25 mL of tetrahydrofuran (THF). The flask was placed in an ice bath at 0 C, and this was followed by the dropwise addition of methacryloyl chloride (MAC; 3 mL, 28.7 mmol, 0.95 eq) via an additional funnel. The reaction was stirred for 24 h at room temperature and then concentrated under reduced pressure, and the excess MAC was removed by dissolution in dichloromethane and washing with deionized water, followed by saturated sodium bicarbonate and finally water. The pure organic layer was dried over magnesium sulfate, filtered, and evaporated to a solid. The pure monomer was recovered by recrystallization with an ethyl acetate/hexane mixture.
- Reaction 5: A 250 mL round bottom flask was charged with a solution mixture of furan (8.32 g, 122 mmol, 1.2 eq), maleic anhydride (10 g, 102 mmol, 1eq), and 80 mL toluene. This solution was left for two days at room temperature after which the precipitated product, exo-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (1), was filtered and washed with cold toluene.
2] About 20.0 g (120 mmol, 1 eq) exo-7-oxabicyclo [2.2.1] hept-5-ene-2,3-dicarboxylic anhydride (1) was dissolved in 150 mL of acetone. 18 mL (16.0 g, 180 mmol, 1.5 eq) of N, N-dimethylaminoethanol was added and the reaction was stirred for 1 h at room temperature. The resulting precipitate was filtered and washed with cold acetone followed by hexane and dried for 2 h in vacuo. The zwitterionic product (B) obtained as a colorless solid, was used without further purification.
- Experiment 6: Complete Spectroscopy characterization of all the molecules synthesized from the reactions 1 to 5.
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