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General procedure: Methyl 3-aryl-2-azidoacrylate 1-11 (20.0 mmol) was added in one portion to a xylene refluxing solution (75 mL) which was heated for 2 h. After evaporation of the solvent, the residue was purified by column chromatography on silica gel using a petroleum ether/EtOAc mixture as eluent. Compounds 12, 18 and 19 were previously described [9b], [13] and [14].
Reference：
[1] European Journal of Medicinal Chemistry, 2012, vol. 49, p. 379 - 396
2
[ 447-61-0 ]
[ 1098340-27-2 ]
Reference：
[1] European Journal of Medicinal Chemistry, 2012, vol. 49, p. 379 - 396
With N-chloro-succinimide; sodium iodide; In N,N-dimethyl-formamide; at 0 - 20℃; for 13.0h;
General procedure: Method B: to a solution of N-chlorosuccinimide (1.2 eq.) in DMF (0.3 M) was added sodium iodide (1.2 eq.) in small portion. The resulting brown solution was stirred at room temperature for 1 h before the slow addition at 0 C of the corresponding indole (1.0 eq.) in DMF (0.3 M). The reaction mixture was stirred at room temperature overnight. A saturated aqueous solution of sodium thiosulfate and water were added and the mixture was stirred for 1 h. After filtration, the crude material was washed with cold water and cold petroleum ether to afford after drying under high vacuum the attempted 3-iodoindole which was used in the next step without any further purification. Compounds 24 (method B), 22-35 (method A) were previously described [11], [18] and [19].
In 5,5-dimethyl-1,3-cyclohexadiene; for 2.0h;Reflux;
General procedure: Methyl 3-aryl-2-azidoacrylate 1-11 (20.0 mmol) was added in one portion to a xylene refluxing solution (75 mL) which was heated for 2 h. After evaporation of the solvent, the residue was purified by column chromatography on silica gel using a petroleum ether/EtOAc mixture as eluent. Compounds 12, 18 and 19 were previously described [9b], [13] and [14].
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