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2b (0.52g; 2.8mmol) was dissolved in 15mL of 98percent hydrazine and stirred under an airflux condenser at 110°C for 8h. The reaction mixture was cooled to rt, and the precipitating crystalline solid was filtered out. The solid was dissolved in EtOAc and was washed with water, a saturated solution of NaHCO3 and brine, followed by evaporation to dryness. The product was purified by column chromatography (gradient:hex/EtOAc 1:1; hex/EtOAc 1:2) to give 0.38g (73percent) of white crystalline solid. Rf=0.53 (CHCl3/MeOH 10:1). mp 166–169°C (lit. 166°C) [63]. IR (KBr): νmax 3280; 1658; 1606; 1588; 1524; 1261; 955cm−1. 1H NMR (300MHz, DMSO): δ 9.69 (s, 1H, NH), 8.35–8.10 (m, 1H, Ar), 8.05–7.88 (m, 2H, Ar), 7.63–7.26 (m, 4H, Ar), 4.60 (s, 2H, NH2). 13C NMR (75MHz, DMSO): δ 168.2, 133.6, 133.3, 130.2, 130.1, 128.4, 126.8, 126.4, 125.6, 125.6, 125.2.
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With pyridine; In tetrahydrofuran; at 70℃; for 1h;
<Synthesis of an Intermediate for the Blue Light-emitting Compound>; In a 500 ml four-necked flask were placed 2.7 g of the light yellow solid matter (the hydrazide), 1.55 g of the ocherous solid matter (the acid chloride), 0.9 g of pyridine, and 33 ml of tetrahydrofuran. The reaction mixture in the four-necked flask was heated to 70C in a silicone oil bath, and allowed to react for 1 hour at around the temperature. After the termination of the reaction, solids in the obtained liquid were separated and washed with water and methanol. The washed solids were dried up, and 2.8 g of an intermediate for the blue light-emitting compound was obtained.
<Synthesis of an Intermediate for the Blue Light-emitting Compound>; 3.5 g (1.37 × 10-2 mole) of the acid chloride represented by formula (38), 2.55 g of the hydrazide represented by formula (19), and 150 ml of tetrahydrofuran were placed in a 500 ml three-necked flask. The mixture in the flask was heated to 70C in a silicone oil bath and allowed to react for 1 hour at around the temperature. After the termination of the reaction, the reaction product was introduced into ice water. The resultant was extracted with 900 ml of chloroform. The chloroform solution was washed twice with 200 ml each of water. The solution was dried with anhydrous sodium sulfate, and filtered. The solvent was removed with an evaporator. 5.5 g of a white solid matter, which was an intermediate represented by formula (39), was obtained.
2b (0.52g; 2.8mmol) was dissolved in 15mL of 98% hydrazine and stirred under an airflux condenser at 110C for 8h. The reaction mixture was cooled to rt, and the precipitating crystalline solid was filtered out. The solid was dissolved in EtOAc and was washed with water, a saturated solution of NaHCO3 and brine, followed by evaporation to dryness. The product was purified by column chromatography (gradient:hex/EtOAc 1:1; hex/EtOAc 1:2) to give 0.38g (73%) of white crystalline solid. Rf=0.53 (CHCl3/MeOH 10:1). mp 166-169C (lit. 166C) [63]. IR (KBr): numax 3280; 1658; 1606; 1588; 1524; 1261; 955cm-1. 1H NMR (300MHz, DMSO): delta 9.69 (s, 1H, NH), 8.35-8.10 (m, 1H, Ar), 8.05-7.88 (m, 2H, Ar), 7.63-7.26 (m, 4H, Ar), 4.60 (s, 2H, NH2). 13C NMR (75MHz, DMSO): delta 168.2, 133.6, 133.3, 130.2, 130.1, 128.4, 126.8, 126.4, 125.6, 125.6, 125.2.
1-Naphthohydrazide (4.0 g, 21.5 mmol) and potassium hydroxide (1.2 g, 21.5 mmol) in ethanol (100 mL) was stirred for 30 min and then carbon disulfide (3.0 mL, 49.4 mmol) was added. The reaction mixture was stirred at room temperature for 4 h. The yellow precipitate was collected by filtration and the product was washed with ether. This product was slowly added to sulfuric acid (20 mL, 375 mmol) at 0 C then stirred at rt for 2 h. The reaction mixture was poured into ice and the product was collected by filtration.Recrystallization from ethanol gave pure yellow product 51 : (3.2 g, 61%). NMR (DMSO- d6) delta 7.60 - 7.74 (m, 3 H), 7.81 (d, J= 7.2 Hz, 1 H), 8.07 (d, J= 7.8 Hz, 1 H), 8.16 (d, J= 8.2 Hz, 1 H) and 8.60 (d, J= 8.2 Hz, 1 H); 13C NMR ( DMSO- 6) delta 124.69, 124.98, 125.42, 126.87, 128.07, 128.78, 129.16, 129.55, 131.83, 133.46, 161.13 and 174.68; HRMS (m/z): [M + Hf calcd. for C12H9N2S2, 245.0202; found, 245.0204.
With potassium hydroxide; In ethanol; at 25℃; for 10.1667h;Reflux; Inert atmosphere;
To a solution of KOH (3.01 g, 53.7 mmol) in ethanol (130 mL) was added naphthalene- 1 -carbohydrazide (5 g, 26.9 mmol); this was stirred at RT for 10 minutes.Carbon disulfide (4 mL, 67.1 mmol) was then added dropwise and the reaction mixture was stirred at reflux for 10 h. Solvent was evaporated under diminished pressure and the residue was neutralized with 10% aq. HC1. The solid product was collected by filtration and recrystallized from ethanol to give pure white crystals of compound 2. .H NMR ( DMSO--4)6 7.63 - 7.77 (m, 3 H), 8.06 - 8.16 (m, 2 H), 8.22 (d, J= 8.2 Hz, 1H) and 8.83 (dd, J= 8.5, 1.1 Hz, 1H); 13C NMR (DMSO- ) 6 118.51, 124.81, 125.32, 126.87, 128.35, 128.51, 128.62 , 129.01, 132.96, 133.34, 160.30 and 176.90; HRMS (m/z): [M + H]+ calcd. for Ci2¾N2OS, 229.0430; found, 229.0432.
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