Chromodihydropyran sulfonamide spiro compound and preparation method thereof
A technology of chroman-like sulfonamide spiro and chroman, which is applied in the field of chroman-like sulfonamide spiro compounds and their preparation, and can solve the problem of undiscovered sulfonamide spiro compounds, etc. problem, to achieve the effect of increasing diversity and improving polarity
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Embodiment 1
[0042] Example 1: 6-bromo-2,2-dimethylspiro[chroman-4-3'-(1,2,5)thiodiazoline]-4'-one-S, Preparation of S-dioxide I-a
[0043]
[0044] Steps:
[0045] 1-(5-bromo-2-hydroxyphenyl)ethanone 1 (570 g, 2.6 mol) was dissolved in 970 ml of acetone (13 mol) and 5.5 liters of toluene in a mixed solution, and then 220 ml of tetrahydro Pyrrole (2.6 mol), stirred at 80°C for 16 hours. The reaction mixture was concentrated into a black oily crude product, which was purified by column chromatography to obtain 544 g of light yellow oily 6-bromo-2,2-dimethylchroman-4-one 2 with a yield of 80%. HNMR (CDCl 3 ) d: 7.84 (s, 1H), 7.42 (d, J = 8.8 Hz, 1H), 6.73 (d, J = 8.8 Hz, 1H), 2.61 (s, 2H), 1.32 (s, 6H).
[0046] 200 g of 6-bromo-2,2-dimethylchroman-4-one 2 (0.78 mol), 550 g of ammonium carbonate (5.5 mol), 104 g of potassium cyanide (1.56 mol) and 1.2 Add ammonium formate into the autoclave. The mixture was stirred at 100°C for 48 hours, then cooled to room temperature and dilut...
Embodiment 2
[0056] Example 2: 6-bromo-2,2,5'-trimethylspiro[chroman-4-3'-(1,2,5)thiodiazoline]-4'-one Preparation of -S,S-dioxide I-b
[0057]
[0058] Steps:
[0059] 359 mg of 6-bromo-2,2-dimethylspiro[chroman-4-3'-(1,2,5)thiodiazoline]-4'-one-S,S - Dioxide I-a (1 mmol), added to a solution in 50 ml of tetrahydrofuran, followed by 60 mg of sodium hydride (60% in mineral oil). The mixture was stirred at room temperature 25°C for 0.5 hours, and then 142 mg of methyl iodide was added to the mixture. The reaction solution was stirred at room temperature for 16 hours and then concentrated. The resulting crude product was separated by column chromatography to obtain 340 mg of 6-bromo-2,2,5 '-Trimethylspiro[chroman-4-3'-(1,2,5)thiodiazoline]-4'-one-S,S-dioxide I-b. Yield: 91%.
[0060] HNMR (DMSO) d: 11.2 (br s, 1H), 7.35 (s, 1H), 7.22 (d, J = 8.8 Hz, 1H), 6.95 (br s, 1H), 6.65 (d, J = 8.8 Hz, 1H), 2.71 (s, 3H), 2.41 (d, J = 14.4 Hz, 1H), 1.88 (d, J = 14.4 Hz, 1H), 1.34 (s, 3H),...
Embodiment 3
[0061] Example 3: 6-bromo-2,2-dimethyl-5'-benzylspiro[chroman-4-3'-(1,2,5)thiodiazoline]-4 Preparation of '-keto-S,S-dioxide 1-c
[0062]
[0063] Steps:
[0064] 359 mg of 6-bromo-2,2-dimethylspiro[chroman-4-3'-(1,2,5)thiodiazoline]-4'-one-S,S - Dioxide I-a (1 mmol), added to a solution in 50 ml of tetrahydrofuran, followed by 60 mg of sodium hydride (60% in mineral oil). The mixture was stirred at room temperature 25°C for 0.5 hours, then 126 mg of benzyl chloride was added to the mixture, the reaction solution was stirred at room temperature for 16 hours and then concentrated. The resulting crude product was separated by column chromatography to obtain 420 mg of 6-bromo-2,2-di Methyl-5'-benzylspiro[chroman-4-3'-(1,2,5)thiodiazoline]-4'-one-S,S-dioxide 1- c. Yield: 93%.
[0065] HNMR (DMSO) d: 7.35 (s, 1H), 7.33-7.29 (m, 3H), 7.22 (d, J = 8.8 Hz, 1H), 7.19 (d, J = 7.6 Hz, 2H), 6.95 (br s, 1 H), 6.65 (d, J = 8.8 Hz, 1H), 4.50 (s, 2H), 2.41 (d, J = 14.4 Hz, 1H)...
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