Syntheses of Furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines and Furo[2`,3`: 5,6]-pyrimido[3,4-b][2,3-e]indolo[1,2,4]triazine as a New Ring System
2-Amino-4,5-di-(2-furyl)furan-3-carbonitrile (1) reacted with triethyl orthoacetate to afford the corresponding 2-ethoxyimine derivative (2). The latter compound reacted with phenyl hydrazine, p-fluorobenzylamine and sodium hydrogen sulfide, respectively, to afford the corresponding furo[2,3-d]pyrim...
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| Format: | Article |
| Language: | English |
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MDPI AG
2000-06-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/5/6/826/ |
| _version_ | 1811269824002654208 |
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| author | Nasser A. Hassan |
| author_facet | Nasser A. Hassan |
| author_sort | Nasser A. Hassan |
| collection | DOAJ |
| description | 2-Amino-4,5-di-(2-furyl)furan-3-carbonitrile (1) reacted with triethyl orthoacetate to afford the corresponding 2-ethoxyimine derivative (2). The latter compound reacted with phenyl hydrazine, p-fluorobenzylamine and sodium hydrogen sulfide, respectively, to afford the corresponding furo[2,3-d]pyrimidine derivatives (3-5). Compound 1 also reacted with carbon disulfide and phenyl isocyanate to afford 5,6-di-(2-furyl)-1H-4H-furo[2,3-d]-[1,3-thiazin]-4-imino-2-thione (6) and 5,6-di-(2-furyl)-1H-3H-3-phenylfuro[2,3-d]pyrimidin-4-imine-2-one (7), respectively. Treatment of compound 2 with hydrazine hydrate at 0oC afforded compound 8, while on boiling 5,6-di-(2-furyl)-3H,4H-4-imino-2-methylfuro-[2,3-d]pyrimidin-3-amine (9) was isolated. Treatment of 9 with carbon disulfide, cyanogen bromide, ethyl cyanoacetate, diethyloxalate and triethyl orthoformate gave the corresponding furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines (10-14). Reaction of 9 with isatin and N-acetyl isatin gave the condensation products 15 and 16 respectively. |
| first_indexed | 2024-04-12T21:50:03Z |
| format | Article |
| id | doaj.art-b1bef877b00142caa75aab8354d807b1 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T21:50:03Z |
| publishDate | 2000-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b1bef877b00142caa75aab8354d807b12022-12-22T03:15:31ZengMDPI AGMolecules1420-30492000-06-015682683410.3390/50600826Syntheses of Furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines and Furo[2`,3`: 5,6]-pyrimido[3,4-b][2,3-e]indolo[1,2,4]triazine as a New Ring SystemNasser A. Hassan2-Amino-4,5-di-(2-furyl)furan-3-carbonitrile (1) reacted with triethyl orthoacetate to afford the corresponding 2-ethoxyimine derivative (2). The latter compound reacted with phenyl hydrazine, p-fluorobenzylamine and sodium hydrogen sulfide, respectively, to afford the corresponding furo[2,3-d]pyrimidine derivatives (3-5). Compound 1 also reacted with carbon disulfide and phenyl isocyanate to afford 5,6-di-(2-furyl)-1H-4H-furo[2,3-d]-[1,3-thiazin]-4-imino-2-thione (6) and 5,6-di-(2-furyl)-1H-3H-3-phenylfuro[2,3-d]pyrimidin-4-imine-2-one (7), respectively. Treatment of compound 2 with hydrazine hydrate at 0oC afforded compound 8, while on boiling 5,6-di-(2-furyl)-3H,4H-4-imino-2-methylfuro-[2,3-d]pyrimidin-3-amine (9) was isolated. Treatment of 9 with carbon disulfide, cyanogen bromide, ethyl cyanoacetate, diethyloxalate and triethyl orthoformate gave the corresponding furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines (10-14). Reaction of 9 with isatin and N-acetyl isatin gave the condensation products 15 and 16 respectively.http://www.mdpi.com/1420-3049/5/6/826/PyrimidinestriazolopyrimidinepyrimidoindolotriazineNMR spectra |
| spellingShingle | Nasser A. Hassan Syntheses of Furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines and Furo[2`,3`: 5,6]-pyrimido[3,4-b][2,3-e]indolo[1,2,4]triazine as a New Ring System Molecules Pyrimidines triazolopyrimidine pyrimidoindolotriazine NMR spectra |
| title | Syntheses of Furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines and Furo[2`,3`: 5,6]-pyrimido[3,4-b][2,3-e]indolo[1,2,4]triazine as a New Ring System |
| title_full | Syntheses of Furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines and Furo[2`,3`: 5,6]-pyrimido[3,4-b][2,3-e]indolo[1,2,4]triazine as a New Ring System |
| title_fullStr | Syntheses of Furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines and Furo[2`,3`: 5,6]-pyrimido[3,4-b][2,3-e]indolo[1,2,4]triazine as a New Ring System |
| title_full_unstemmed | Syntheses of Furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines and Furo[2`,3`: 5,6]-pyrimido[3,4-b][2,3-e]indolo[1,2,4]triazine as a New Ring System |
| title_short | Syntheses of Furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines and Furo[2`,3`: 5,6]-pyrimido[3,4-b][2,3-e]indolo[1,2,4]triazine as a New Ring System |
| title_sort | syntheses of furo 3 2 e 1 2 4 triazolo 1 5 c pyrimidines and furo 2 3 5 6 pyrimido 3 4 b 2 3 e indolo 1 2 4 triazine as a new ring system |
| topic | Pyrimidines triazolopyrimidine pyrimidoindolotriazine NMR spectra |
| url | http://www.mdpi.com/1420-3049/5/6/826/ |
| work_keys_str_mv | AT nasserahassan synthesesoffuro32e124triazolo15cpyrimidinesandfuro2356pyrimido34b23eindolo124triazineasanewringsystem |