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Synthesis of o-Sulfamidotriazobenzenes from 1,1‘-Sulfonylbis(benzotriazole)

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posted on 20.07.2007, 00:00 by Alan R. Katritzky, Levan Khelashvili, Khanh N. B. Le, Prabhu P. Mohapatra, Peter J. Steel
Easily accessible 1,1‘-sulfonylbis(benzotriazole) (Bt2SO2, 1) reacts with secondary amines at room temperature to afford (i) the corresponding o-sulfamidotriazobenzenes 2ad (53−75%) via concurrent substitution of the first and ring opening of the second benzotriazolyl group and (ii) N-sulfonylbenzotriazoles 3b,c,e,f (7−73%). 1-(Morpholine-4-sulfonyl)-1H-benzotriazole 3c reacts with piperidine, pyrolidine, and N-methylpiperazine under microwave irradiation (120 W) at 120 °C for 10 min to give the unsymmetrical sulfamides 4ac (80−90%).

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