Synthesis and antimicrobial activity of [1,2,5]thiadiazolo-[3,4-g]indoles


T h e s t a r t i n g 4 a m i n o 2 , 1 , 3 b e n z o t h i a d i a z o l e ( I ) w a s o b t a i n e d f r o m 2 , 1 , 3 . b e n z o t h i a d i a z o l e ( p i a z t h i o l e ) b y a s t a n d a r d m e t h o d [ 7 ] . D i a z o t i z a t i o n o f t h e a m i n e ( I ) w i t h : ; o d i u m n i t r i t e in conc. hydrochloric acid followed by reduction of the diazonium salt with stannous chloride gave the tin complex of 4-hydrazino-2,1,3-benzothiadiazole (II), which on heating in hydrochloric acid with ketones of general formula RCH2COR' gave the required compounds (IVc-h). In the synthesis of (IVa, b), the intermediate acetone and acetophenone 4(2, I, 3-benzothiadiazolyl)hydrazones (IIIa, b) were isolated and cyclized to the thiadiazoloindoles (IVa, b) by heating in polyphosphoric acid.

DOI: 10.1007/BF00757963

Cite this paper

@article{Titov2004SynthesisAA, title={Synthesis and antimicrobial activity of [1,2,5]thiadiazolo-[3,4-g]indoles}, author={G . A . Titov and V. P. Chetverikov and Yu. G. Bundel' and O. A. Malyuga and T. I. Ivchenko and E. N. Alekseeva}, journal={Pharmaceutical Chemistry Journal}, year={2004}, volume={21}, pages={867-870} }