Synthesis and Antimicrobial Activity of 4-Amino-3-(2'-phenylindol-3'-yl) - 2-imino-4-thiazoline-5-carbonitriles and their Derivatives
| Main Authors: | S. P. HIREMATH, K. M. K. SWAMY, B. H. M. MRUTHYUNJAYASWAMY |
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| Format: | Article Journal |
| Bahasa: | eng |
| Terbitan: |
, 1992
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| Subjects: | |
| Online Access: |
https://zenodo.org/record/5993138 |
Daftar Isi:
- Department of Chemistry, Gulbarga University, Gulbarga-585 106 Manuscript received 19 August 1991, accepted 17 February 1992 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 (la - c). These thioureas on condensation with bromoamalononitrile afforded 4-amino-3-(2'-phenylindo1-3'-y1)-2-imino-4-thiazoline-5-carbonitriles (2a - C.) On acetylation with acetic anhydride and glacial acetic acid at room temperature, as well as on heating, 2a - c yielded only 4-acetylamino-3-(2'-phenylindo1-3`-y1)-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'-phenylindo1-3'-y1)-2-imino-4-thiazoline-5-carboxamides (4a - c), and under similar conditions, 4-amino-3-(2'-phenylindo1-3'-y1)-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'-phenylindo1-3'-y1)-2-imino-4-thiazoline-5-carbonitriles (6a - c) and 4-phenylureido-3-(2'-phenylindo1-3'-y1)- 2-imino-4-thiazoline-4-carbonitriles (7a—c), respectively.