SYNTHESIS OF IMIDAZO[4,5-C] AND TRIAZEPINO|6,5-C]CINNOLINES | ||
Zagazig Journal of Pharmaceutical Sciences | ||
Article 1, Volume 9, Issue 2, December 2000, Pages 1-6 PDF (2.95 M) | ||
Document Type: Original Article | ||
DOI: 10.21608/zjps.2000.169703 | ||
Authors | ||
Khadiga Ghoneim* ; Mohamed Essawi; Salwa El-Meligie; Aliaa Kamal | ||
Department of Organic Chemistry, Faculty of Pharmacy, Cairo University, Kasr-El-Ainy 11562, Cairo, Egypt. | ||
Abstract | ||
Hofmann degradation of 4-amino-8-methylcinnoline-3-carboxamide (1) gave 3,4-diaminocinnoline 2 which was employed to prepare imidazo and 2-substitutedimidazo[4,5-c]cinnolines 3. On the other hand, reaction of 4-aminocinnoline-3-carboxylic acid hydrazides 4 with ethyl chloroformate or potassium O-ethyl dithiocarbonate afforded 2,3,4,5-tetrahydro-1H-1,2,4- triazepino[6,5-c]cinnoline-2,5-diones 6 and the corresponding 2-thiones 7, respectively. Furthermore, reacting 4 with excess orthoesters gave mixtures of 4,5-dihydro-1H-1,2,4-triazepino[6,5-c]cinnolin-5-ones 9 and 3-(ethoxyalkylidenamino) pyrimi-do[5,4-c] cinnoline-4-ones 10 which were separated and characterized. | ||
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