Novel Synthesis and Characterization of Azoles, Azines and Azepines Based on Cinnamoyl Thiourea Derivatives | ||||
| Egyptian Journal of Chemistry | ||||
| Volume 66, Issue 13, December 2023, Page 1791-1800 PDF (278.21 K) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/ejchem.2023.243272.8798 | ||||
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| Author | ||||
Islam Ragab  
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| Department of Mathematics, College of Science and Arts, Qassim University, Riyadh Al Khabra, Saudi Arabia | ||||
| Abstract | ||||
| (Acryloyl)thioureido)benzoic acid) derivative 3a-c was obtained by reacting cinnamoyl isothiocyanate 2a-c with 2-aminobenzoic acid 1. The cyclization of thiourea 3a-c in dry acetone yielded 2-mercapto-4-oxopyrimidine 4a-c, while in ethoxide, it led to the formation of quinoxaline 5a-c and (Z)-2-(6-(4-nitrophenyl)-4-oxo-5-phenyl-3,4-dihydro-2H-1,3-thiazin-2-ylideneamino)benzoic acid 6c. (E)-2-(3-(2,4-dichlorophenyl)acryloyl)-1-thioxo-2,2a,2a1,4a-tetrahydro-4H-3-oxa-2,9b-diazapentaleno[1,6-ab]naphthalene-4,5(1H)-dione 11a was obtained by reacting thiourea 3a with maleic anhydride. Refluxing thiourea 3a with chloroacetamide resulted in the production of (Z)-2-((4-(2,4-dichlorostyryl)-6-oxo-6,7-dihydro-1,3,5-thiadiazepin-2-yl)amino)benzoic acid 13a and 2-(((Z)-5-carbamoyl-4-((E)-2,4-dichlorostyryl)thiazolidin-2-ylidene)amino)benzoic acid 15a and its isomeric form depending on the base medium. Alkylation of thiourea 3a with ethyl bromoacetate afforded 2-(((Z)-(((E)-3-(2,4-dichlorophenyl)acryloyl)imino)((2-ethoxy-2-oxoethyl)thio)methyl)amino)benzoic acid 16a, which reacted with hydrazine hydrate to yield 12-(2,4-dichlorophenyl)-6,7a-dihydro-7H,10H-benzo[d]pyrazolo[3,4-f]pyrimido[2,1-b][1,3]thiazepine-7,10-dione 17a. Treatment of thiourea 3a with H2O2 in basic and/or acidic medium yielded (E)-2-(3-(3-(2,4-dichlorophenyl)acryloyl)ureido)benzoic acid 18a and (E)-2-(((3-(2,4-dichlorophenyl)acrylamido)methyl)amino)benzoic acid 19a , respectively. The structures of the newly synthesized compounds were verified by analyzing their FT-IR, 13C-NMR, and 1H-NMR spectra. | ||||
| Keywords | ||||
| Synthesis(chemical); thiopyrimidin; thiazine; Imidazole; thiazole; pyrimidothiazepine | ||||
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