144106-93-4Relevant articles and documents
Synthesis and Antimicrobial Activity of 4-Amino-3-(2'-phenylindol-3'-yl)-2-imino-4-thiazoline-5-carbonitriles and their Derivatives
Hiremath, S. P.,Swamy, K. M. K.,Mruthyunjayaswamy, B. H. M.
, p. 87 - 89 (2007/10/02)
2-Phenyl-3-aminoindoles on reaction with benzoyl isothiocyanate furnished the respective N-(2-phenyl-3-indolyl)-N'-benzoylthioureas, which on hydrolysis with alcoholic sodium hydroxide gave 2-phenyl-3-indolylthioureas (1a-c).These thioureas on condensation with bromomalononitrile afforded 4-amino-3-(2'-phenylindol-3'-yl)-2-imino-4-thiazoline-5-carbonitriles (2a-c).On acetylation with acetic anhydride and glacial acetic acid at room tempearature, as well as on heating, 2a-c yielded only 4-acetylamino-3-(2'-phenylindol-3'-yl)-2-imino-4-thiazoline-5-carbonitriles (3a-c) but not the diacetyl derivatives (2a-c).Compounds 3a-c on heating with orthophosphoric acid followed by basification with aqueous ammonia afforded 4-acetylamino-3-(2'-phenylindol-3'-yl)-2-imino-4-thiazoline-5-carboxamides (4a-c), and under similar conditions, 4-amino-3-(2'-phenylindol-3'-yl)-2-imino-4-thiazoline-5-carboxamides (5a-c) were obtained directly from 2a-c.Compounds 2a-c on condensation with various isothiocyanates and phenylisocyanate yielded 4-alkyl/(p-substituted)-phenylthioureido-3-(2'-phenylindol-3'-yl)-2-imino-4-thiazoline-5-carbonitriles (6a-c) and 4-phenylureido-3-(2'-phenylindol-3'-yl)-2-imino-4-thiazoline-4-carbonitriles (7a-c), respectively.
