مورد إلكتروني
Regioselective synthesis of pyrimido [1,2-a][1,3,5]triazin-6-ones via reaction of 1-(6-oxo-1,6-dihydropyrimidin-2-yl)guanidines with triethylorthoacetate: Observation of an unexpected rearrangement
| العنوان: | Regioselective synthesis of pyrimido [1,2-a][1,3,5]triazin-6-ones via reaction of 1-(6-oxo-1,6-dihydropyrimidin-2-yl)guanidines with triethylorthoacetate: Observation of an unexpected rearrangement |
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| بيانات النشر: | The Royal Society of Chemistry 2012 |
| تفاصيل مُضافة: | Sachdeva, N. Dolzhenko, Anton Chui, W. |
| نوع الوثيقة: | Electronic Resource |
| مستخلص: | A novel thermal rearrangement, involving pyrimidine ring opening and subsequent ring closure leading to recyclization of the system, was identified in the reaction of (6-oxo-1,6- dihydropyrimidin-2-yl)guanidines 3 (where NR1R2 = NH2, NH alkyl, NH aralkyl, NHCH2Ph(R)) with triethyl orthoacetate, affording 4-substituted-2-methyl-6H-pyrimido[1,2-a][1,3,5]triazin-6- ones 6 and their ring opened products. However, no such rearrangement was observed with (6- oxo-1,6-dihydropyrimidin-2-yl)guanidines 3 bearing a tertiary amino or anilino substituent (i.e. where NR1R2 = N(CH3)2, indoline, morpholino, NHAr). As expected, 2-substituted-4-methyl- 6H-pyrimido[1,2-a][1,3,5]triazin-6-ones 4 were obtained as the final products. Experimental 2 structural determination and theoretical studies were carried out to get an understanding of the observed thermal rearrangement. In addition, an attempt to obtain similar pyrimido[1,2-a][1,3,5]triazin-6-ones using N,N-dimethylacetamide dimethyl acetal (DMA-DMA) as one carbon inserting synthon had furnished triazine ring annulated product 14 bearing N,N-dimethyl enamino substituent at position 4 as a result of further reaction with a second molecule of DMA-DMA. |
| مصطلحات الفهرس: | 3, X-ray crystal structure, triazines, 2-a][1, guanidines, pyrimido[1, 5]triazines, rearrangement, pyrimidines, Journal Article |
| URL: | |
| الإتاحة: | Open access content. Open access content |
| أرقام أخرى: | LC0 oai:espace.curtin.edu.au:20.500.11937/10305 Sachdeva, Nikhil and Dolzhenko, Anton and Chui, Wai Keung. 2012. Regioselective synthesis of pyrimido [1,2-a][1,3,5]triazin-6-ones via reaction of 1-(6-oxo-1,6-dihydropyrimidin-2-yl)guanidines with triethylorthoacetate: Observation of an unexpected rearrangement. Organic & Biomolecular Chemistry. 10 (23): pp. 4586-4596. 10.1039/C2OB25195G 1033947235 |
| المصدر المساهم: | CURTIN UNIV OF TECH From OAIster®, provided by the OCLC Cooperative. |
| رقم الأكسشن: | edsoai.on1033947235 |
| قاعدة البيانات: | OAIster |
| الوصف غير متاح. |