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A novel series of 4-aryl-2-cyanoimino-3,4-dihydro-1H-pyrimidines (aryl-CIDHPMs) was synthesized using a new method via the one-pot three-component reaction of cyanoguanidine with malononitrile and aromatic aldehydes using sodium methoxide as catalyst. These new aryl-CIDHPMs were also prepared by a classical route via reaction of cyanoguanidine with the corresponding arylidenemalononitriles under our conditions. In the same manner, the reaction of cyanoguanidine with cyclohexylidenemalononitrile and/or isatinylidenemalononitrile afforded new spiro-pyrimidines 9 and 10, respectively. A new series of polyfunctionalized 2-cyanoaminopyrimidines was obtained from the reaction of cyanoguanidine with cinnamaldehyde and/or ethoxyalkylenemalononitriles.

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List of contents 1. General Information……………………………………………………………….……………………S3 2. Procedure for the Synthesis of 4-Amino-5-hydrazino-4H-[1,2,4]-triazole-3-thiol (1)…………..……..S4 3. Characterization Data of 4-Amino-5-hydrazino-4H-[1,2,4]-triazole-3-thiol (1)..………..…………….S4 4. 1 H and 13 C NMR Spectra of 1………...……………………………………………………..………S5-S6 5. General Procedure for the Synthesis of 4 and 6-8…………………………………………………..…S7 6. Characterization Data of 4 and 6-8……………………………………….………...………….….S7-S45 S2 EXPERIMENTAL 1. General Information: All commercially available reagents were purchased from Merck, Aldrich and Fluka and were used without further purification. All reactions were monitored by thin layer chromatography (TLC) using precoated plates of silica gel G/UV-254 of 0.25 mm thickness (Merck 60F254) using UV light (254 nm/365 nm) for visualization. Melting points were detected with a Kofler melting points apparatus and uncorrected. Infrared spectra were recorded with a FT-IR-ALPHBROKER-Platinum-ATR spectrometer and are given as cm-1 using the attenuated total reflection (ATR) method. 1 H NMR and 13 C NMR spectra for all compounds were recorded in DMSO-d 6 on a Bruker Bio Spin AG spectrometer at 400 MHz and 100 MHz, respectively. 1 H NMR, chemical shifts (δ) were given in parts per million (ppm) with reference to tetramethylsilane (TMS) as an internal standard (δ=0); coupling constants (J) were given in hertz (Hz) and data are reported as follows: chemical shift, integration, multiplicity (s=singlet, d=doublet, t= triplet, q=quartet, m=multiplet). For 13 C NMR, TMS (δ=0) or DMSO (δ=39.51) was used as internal standard and spectra were obtained with complete proton decoupling. Elemental analyses were obtained on a Perkin-Elmer CHN-analyzer model. S3 3. Characterization Data of 4-Amino-5-hydrazino-4H-[1,2,4]-triazole-3-thiol (1): A mixture of thiourea (0.5 mole, 38g) and 98% hydrazine hydrate (100 ml), were refluxed in water bath for 3hrs. The reaction mixture was cooled, diluted with 150 ml dist. water, neutralized (pH~ 6.5) by addition 10 ml HCl (2M)and refrigerated at 0 o C for 30 min. The crude product was filtered, washed with cold water and digested in dilute HCl (2M, 375 ml) for 15 min. After removal of acid-insoluble impurities, the filtrate was neutralized to pH ~ 6.5 with NaOH and