Hemming, Karl, Chambers, Christopher Steven, Hamasharif, Muslih S., Joãoa, Heidi, Khan, Musharraf N., Patel, Nilesh, Airley, Rachel and Day, Sharn (2014) Azide based routes to tetrazolo and oxadiazolo derivatives of pyrrolobenzodiazepines and pyrrolobenzothiadiazepines. Tetrahedron, 70 (40). pp. 7306-7317. ISSN 0040-4020
Abstract

Tetrazolo- and 1,2,4-oxadiazolo-fused derivatives of the antitumour, antibiotic, DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines and their pyrrolobenzothiadiazepine derivatives have been produced as analogues of a 1,2,3-triazolo-fused pyrrolobenzothiadiazepine which was shown to be a Glut-1 transporter inhibitor with potential as an antitumour agent. The tetrazolo-fused systems were produced by intramolecular 1,3-dipolar cycloaddition between an azide and a nitrile. The 1,2,4-oxadiazolo systems were produced by nitrile oxide cycloadditions to pyrrolobenzothiadiazepines which were in turn produced from a 2-(azidobenzenesulfonyl)-1,2-thiazine 1-oxide. The latter species underwent a phosphite mediated one-pot sulfur extrusion, ring contraction and azide to amine conversion to form 1-(aminobenzenesulfonyl)pyrroles. Bischler-Napieralski ring closure gave the pyrrolobenzothiadiazepines.

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