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Molecules 2000, 5(6), 826-834; doi:10.3390/50600826
Article

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

National Research Centre, Dokki, Cairo, Egypt
Received: 13 January 2000 / Accepted: 10 May 2000 / Published: 24 June 2000
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Abstract

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.
Keywords: Pyrimidines; triazolopyrimidine; pyrimidoindolotriazine; NMR spectra Pyrimidines; triazolopyrimidine; pyrimidoindolotriazine; NMR spectra
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Hassan, N.A. 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 2000, 5, 826-834.

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