Synthesis of o-sulfamidotriazobenzenes from 1,1'-sulfonylbis(benzotriazole)

Alan R Katritzky; Levan Khelashvili; Khanh N B Le; Prabhu P Mohapatra; Peter J Steel

doi:10.1021/jo0705723

Synthesis of o-sulfamidotriazobenzenes from 1,1'-sulfonylbis(benzotriazole)

J Org Chem. 2007 Jul 20;72(15):5805-8. doi: 10.1021/jo0705723. Epub 2007 Jun 21.

Authors

Alan R Katritzky¹, Levan Khelashvili, Khanh N B Le, Prabhu P Mohapatra, Peter J Steel

Affiliation

¹ Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA. katritzky@chem.ufl.edu

PMID: 17583958
DOI: 10.1021/jo0705723

Abstract

Easily accessible 1,1'-sulfonylbis(benzotriazole) (Bt2SO2, 1) reacts with secondary amines at room temperature to afford (i) the corresponding o-sulfamidotriazobenzenes 2a-d (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 degrees C for 10 min to give the unsymmetrical sulfamides 4a-c (80-90%).