Academic Journal
Fluorine-Containing Heterocycles: Part I. Synthesis of New 7-(2-thienyl)-9-Trifluoromethylpyrido[3′,2′:4,5]Thieno[3,2-d]Pyrimidines and Related Fused Tetracyclic Systems
| العنوان: | Fluorine-Containing Heterocycles: Part I. Synthesis of New 7-(2-thienyl)-9-Trifluoromethylpyrido[3′,2′:4,5]Thieno[3,2-d]Pyrimidines and Related Fused Tetracyclic Systems |
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| المؤلفون: | Bakhite, Etify A., Abdel-Rahman, Abdu E., Al-Taifi, Elham A. |
| المصدر: | Journal of Chemical Research ; volume 2005, issue 3, page 147-154 ; ISSN 1747-5198 2047-6507 |
| بيانات النشر: | SAGE Publications |
| سنة النشر: | 2005 |
| الوصف: | 3-amino-6-(2-thienyl)-4-trifluoromethylthieno[2,3-b]pyridine-2-carboxamide (3) and 2-carbonitrile analogue 5 were prepared by reaction of 3-cyano-6-(2-thienyl)-4-trifluoromethylpyridine-2(1H)-thione (1) with chloroacetamide or chloroacetonitrile respectively. Heating compound 3 with triethyl orthoformate led to the formation of pyridothienopyrimidinone derivative 6. Reaction of 6 with phosphorus oxychloride produced 4-chloropyrimidine derivative 7 which underwent some nucleophilic displacements upon treatment with thiourea, piperidine, morpholine or hydrazine hydrate to give the target 4-substituted pyridothienopyrimidines 8, 10a, 10b and 11 respectively. Reaction of compound 8 with methyl iodide or ethyl chloroacetate gave compounds 9a,b. The condensation of 3-amino-6-(2-thienyl)-4-trifluoromethyl-thieno[2,3-b]pyridine-2-carbonitrile (5) with triethyl orthoformate led to the formation of methanimidate derivative 21 which upon treatment with hydrazine hydrate gave the target 3-amino-3,4-dihydro-4-imino-7-(2-thienyl)-9-trifluoromethylpyrido[3′,2′:4,5] thieno[3,2-d]pyrimidine (22). The reactions of compounds 11 and 22 with some reagents namely; triethyl orthoformate, acetic anhydride, formic acid, acetic acid, acetylacetone benzaldehyde and/or diethyl malonate were carried out and their products were identified, in most cases as [1,2,4]triazolopyridothienopyrimidines via Dimroth rearrangement. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| DOI: | 10.3184/0308234054213726 |
| الاتاحة: | http://dx.doi.org/10.3184/0308234054213726 http://journals.sagepub.com/doi/pdf/10.3184/0308234054213726 |
| Rights: | http://journals.sagepub.com/page/policies/text-and-data-mining-license |
| رقم الانضمام: | edsbas.B6A9F763 |
| قاعدة البيانات: | BASE |
| DOI: | 10.3184/0308234054213726 |
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