General Papers ARKIVOC 2004 (i) 71-78

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General Papers ARKIVC 2004 (i) 71-78 Synthesis of 1,3,5-triazepine-2,4-dione, pyrrolo[3,4-f] [1,3,5]triazepine-2,4-dione, pyridazino[4,5-f][1,3,5]triazepine and 1,3,5,7,9-pentazaheptaline derivatives.. Abdel-Razik Chemistry Department, Faculty of Science, Mansoura University, ew Damietta 34517, Egypt E-mail: amada600@yahoo.co.uk (received 26 Jan 04; accepted 12 May 04; published on the web 17 May 04) Abstract The reaction of the enaminonitrile 1 with chlorocarbonyl isocyanate 2 afforded the carbonyl isocyanate derivative 3. The 1,3,5-triazepine-2,4-dione derivative 4 was synthesized by refluxing 3 with sodium hydroxide. Compound 4 was used in ring formation through reactions with aliphatic-, aromatic-, and heteroaromatic amines, affording pyrrolo[3,4-f][1,3,5]triazepine, pyridazino[4,5-f][1,3,5]triazepine and 1,3,5,7,9-pentazaheptaline derivatives. Keywords: Enaminonitriles, 1,3,5-triazepine-2,4-dione, pyrrolotriazepine, pyridazinotriazepine, 1,3,5,7,9-pentazaheptaline Introduction The reactions of diaminomaleonitrile (DAM) with diones, 1 isocyanates, 2 and phenylacetyl isothiocyanate 3 have been reported. The corresponding dihydro analogues (C6 C7) of the title ring systems have been described. 4 6 Pyrrolo[3,4-f][1,3,5]triazepine was synthesized by reaction of the amidine derivative of diaminomaleonitrile with carbonyl compounds. 7,8 Chlorocarbonyl isocyanate 2 was used in the synthesis of heterocyclic compounds. 9 12 2 C 1 2 C + Cl 2 2 3 C C 4 C C Scheme 1. The reaction of diaminomaleonitrile with chlorocarbonyl isocyanate. ISS 1424-6376 Page 71

General Papers ARKIVC 2004 (i) 71-78 Results and Discussion The reaction of diaminomaleonitrile 1 with chlorocarbonyl isocyanate 2 in the presence of triethylamine afforded compound 3 whose IR spectra revealed bands at 2265 and 3260 assignable to =C= and 2 groups respectively. Compound 3 was refluxed in the presence of 10% sodium hydroxide to afford 4 whose IR spectra showed the absence of bands assignable to =C= and 2 groups, and its structure is in agreement with its elemental analysis and spectral data. (Scheme 1, and Experimental Section). A B 6 7 C 2 C 2 2.Cl 5a 2 C 2 C 2 5b 4 2 C 5e C 2 5f 10 11 8 S 2 5c S C 2 5g 12 9 S 2 S 5d 2 C 5h 13 Scheme 2. Reactions of compound 4 with aliphatic-, aromatic-, and heteroaromatic amines. ISS 1424-6376 Page 72

General Papers ARKIVC 2004 (i) 71-78 Several 7-substituted-6,8-diimino-2,5-pyrrolo[3,4-f][1,3,5]triazepine-2(1),4(3,5)- dione derivatives 6 9 were prepared by reaction of compound 4 with aliphatic-, aromatic-, and heteroaromatic amines 5a d (Scheme 2). Thus, compound 4 reacted with hydroxylamine hydrochloride 5a in boiling ethanol affording 6 through the intermediate A. The MS of compound 6 was consistent with a parent peak at M + = 210. Also, the product showed no C absorbance but did have an absorbance in the IR consistent with 6. Similarly, compound 4 reacted with ethanolamine 5b in the presence of pyridine, affording 7. Compound 4 reacted with 4-aminothiophenol, 5c, in the presence of pyridine/water to give 8. Also, the reaction of 4 with 2-aminothiazole 5d afforded 9. The structures of the prepared compounds are in agreement with their spectral data (Scheme 2, c.f. Experimental Section). n the other hand, the tetracyclic derivatives 10 13 containing pyrrolo[3,4- f][1,3,5]triazepine-2(1),4(3,5)-dione were synthesized by reaction of 4 with the aromatic and heteroaromatic amines 5e h. Thus, compound 4 reacted with anthranilic acid, 5e affording 10 through the intermediate B. The 1 MR spectra of compound 10 revealed two signals as a pair of doublets at δ = 7.68 (J = 6.65, 6.65 z) and δ = 7.78 (J = 7.7, 7.7 z) and two signals as doublets at δ = 7.84 (J = 7, 5 z) and δ = 8.35 (J = 8, 7 z) for aromatic hydrogens. Similarly, compound 4 reacted with 2-aminobenzonitrile 5f affording 11. Also, compound 4 reacted with 2- aminopyridine-2-carboxylic acid 5g to yield 12 for which 1 MR spectra revealed one signal as pair of doublets at δ = 7.62 (J = 5, 7 z) and two signals as doublet quartet at δ = 8.90 (J = 5, 2 z) and δ = 8.75 (J = 7, 2 z) as a result of meta coupling of pyridine ring hydrogens. Compound 4 reacted with 3-aminopyrazine-2-carboxylic acid 5h affording 13 whose structure is in agreement with its elemental analysis and spectral data (Scheme 2, cf. Experimental). Pyridazino[4,5-f][1,3,5]triazepine-2(1),4(3,5)-dione 14 was synthesized by treatment of 4 with hydrazine hydrate 5 i. Compound 14 was treated with triethyl orthoformate 5j yielding the imidate derivative C which cyclizes under the reaction condition to yield 15. Compound 4 reacted with urea 5k and thiourea 5l to yield 1,3,5,7,9-pentazaheptaline derivatives 16 and 17 respectively. Compound 4 reacted with PCl 3 5m to yield 3-hydro-2,4-dichloro-6,7-dicyano-1,3,5- triazepine 18 for which IR spectra revealed a characteristic nitrile absorption at 2230 cm -1 besides an absorption band at 698 cm -1 for (C Cl) and its elemental analysis and spectral data revealed a molecular formula C 6 5 Cl 2 (M + = 214). ISS 1424-6376 Page 73

General Papers ARKIVC 2004 (i) 71-78 C 2 5 2 2. 2 5i 14 2 2 C(C 2 5 ) 3 5j C 2 5 4 X 2 -C- 2 5k, X = 5l, X = S PCl 3 5m Cl Cl 2 2 16, X = 17, X = S 18 C C X C 15 Scheme 3. ew compounds derived from compound 4. Experimental Section General Procedures. Melting points were determined on a Gallenkamp Electrothermal apparatus and are uncorrected. IR spectra were recorded on a Pye-Unicam SP 110 spectrophotometer, in KBr disks. The 1 - and 13 C- MR spectra were recorded on a Varian Gemini MR spectrometer 300 (300 Mz for 1, 75.5 Mz for 13 C) using Me 4 Si as an internal reference, and are given as δ/ppm. Mass spectra were measured on a itachi 80-B spectrometer at 70 ev. The progress of the reaction was monitored by TLC using precoated silica gel plates (F254, Merck, Darmstadt). Methylene chloride was dried over molecular sieves, 80 100 mesh, and distilled by refluxing over calcium hydride. Preparation of carbonyl isocyanate derivative 3. An equimolar mixture of diaminomaleonitrile 1 (1.08g, 0.01mole) and chlorocarbonyl isocyanate 2 (1.05 g, 0.01 mole) in dry methylene chloride (30 ml) was stirred in the presence of triethylamine (1.5 ml) at 0 C for ISS 1424-6376 Page 74

General Papers ARKIVC 2004 (i) 71-78 2h, then for 1 h at 25 o C and the reaction mixture was left to stand overnight at room temperature. Water (3 ml) was added and the solid product was collected by filtration and crystallized from ethanol. 3: 1.57 g (94 %), m.p. = 276 o C; IR ν/ cm -1 : 2226 (C), 1670 (C), 3430 (), 3260 ( 2 ) 1660 (C=C), 2265 (=C=); 1 MR (CDCl 3 ) δ: 8.2 (br, s, 1, ), 6.4 (br, s, 2, 2 ), D 2 -exchangeable; 13 C MR (CDCl 3 ) δ: 117.2 (C), 117.3 (C), 144.5 (C), 144.7 (C), 165.8 (C), 168.2 (C); m/z: 177 (M +, 82 %). Anal. Calc. for C 6 3 5 2 (MW = 177.12): C 40.69, 1.71, 39.54. Found: C 40.64, 1.67, 39.48 %. Preparation of 6,7-dicyano-1,3,5-triazepine-2(1),4(3,5)-dione (4). To a suspension of compound 3 (1.77 g, 0.01 mol) in methylene chloride was added 10 % a (20 ml). The reaction mixture was refluxed for 2 h and then cooled to room temperature. Water (3 ml) was added and the solid product was collected by filtration and crystallized from ethanol. 4: 1.57 g (89 %), m.p. > 300 o C (ethanol); IR (KBr) ν/ cm -1 : 2228 (C), 1675 (C), 3445 (), 1652 (C=C); 1 MR (CDCl 3 ) δ/ppm: 7.8, 8.0 (br, s, 3, ) D 2 exchangeable; 13 C MR (CDCl 3 ) δ: 117.8 (C), 144.3 (2 x C), 163.8 (C); m/z: 177 (M +, 66 %). Anal. Calc. for C 6 3 5 2 (MW = 177.12): C 40.69, 1.71, 39.54, Found: C 40.64, 1.67, 39.48 % Preparation of 7-substituted-2,5-pyrrolo[3,4-f][1,3,5]triazepine-2(1),4-(3,5)-diones, 6 13 A mixture of 4 (1.77 g, 0.01 mole) and an aliphatic or heteroaromatic amine 5a h (0.01 mole) in 50 ml of (ethanol for 6, pyridine/water for 8, pyridine for 7, 9 13) containing triethylamine (1.5 ml) was refluxed for 3 h. The reaction mixture was cooled. Water was added and the product was filtered, washed with water and crystallized from the appropriate solvent. 7-ydroxy-6,8-diimino-2,5-pyrrolo[3,4-f][1,3,5]triazepine-2-(1), 4-(3,5)-dione (6). Yield 1.78 g (85 %), m.p. = 293 o C (ethanol); IR ν/ cm -1 : 1674 (C), 3448 (), 3350 (C=), 1640 (C=C), 3590 (); 1 MR (CDCl 3 ) δ/ppm: 7.8, 7.3 (br, s, 3, ), 5.3 (s, 2, -C=) D 2 exchangeable, 6.7 (s,, ); 13 C MR (CDCl 3 ) δ: 136.8 (C), 137.6 (C), 142.6 (C), 143.3 (C), 162.4 (C), 162.9 (C); m/z: 210 (M +, 77 %). Anal. Calc. for C 6 6 6 3 (MW = 210.15): C 34.29, 2.88, 39.99, Found: C 34.23, 2.86, 39.95 %. 7-(2-ydroxyethyl)-6,8-diimino-2,5-pyrrolo-[3,4-f][1,3,5]triazepine-2(1),4-(3,5)- dione (7). Yield 1.89 g (77 %), m.p. = 281 o C (ethanol); IR (KBr) ν/ cm -1 : 1680 (C), 3452 (), 3346 (C=), 1644 (C=C), 3470 (); 1 MR (CDCl 3 ) δ/ppm: 7.7, 7.3 (br, s, 3, ), 5.5 (s, 2, -C=), 2.3 (dd, J = 4.1 z, J = 8.7 z,, ) D 2 exchangeable, 2.30-2.33 (m, 2, C 2 ), 3.45 (tt, J = 7.3 z, 1.0 z, 2, C 2 ); 13 C MR (CDCl 3 ) δ: 17.4 (-C 2 ), 18.6 (-C 2 ), 134.4 (C), 135.8 (C), 142.9 (C), 143.5 (C), 162.3 (C), 162.5 (C); m/z: 208 (M +, 85 %). Anal. Calc. for C 7 8 6 2 (MW = 208.18): C 40.39, 3.87, 40.37, Found: C 40.32, 3.79, 40.33 %. 7-(p-Mercaptophenyl)-6,8-diimino-2,5-pyrrolo[3,4-f][1,3,5]triazepine-2(1),4-(3,5)- dione (8). Yield 2.5 g (83 %), m.p. > 300 o C (ethanol); IR (KBr) ν/ cm -1 : 1682 (C), 3454 (), 3348 (C=), 2570 (S), 1642 (C=C); 1 MR (CDCl 3 ) δ/ppm: 7.8, 7.2 (br, s, 3, ), 5.4 (s, 2, -C=), D2 exchangeable, 7.78 (d, J = 7.7 z, 1, Ph), 7.84 (d, J = 7.5 z, 1, Ph), 8.35 ISS 1424-6376 Page 75

General Papers ARKIVC 2004 (i) 71-78 (d, J = 8.7 z, 1, Ph), 8.36 (d, J = 8.2 z, 1, Ph), 3.7 (s, 1, S); 13 C MR (CDCl 3 ) δ: 129.6, 130.4, 131.5, 132.8 (C), 134.9, 135.2, (C) 142.4 (C), 143.2 (C), 144.6 (C), 144.9 (C), 162.8, 163.2 (2 x C); m/z: 302 (M +, 62 %). Anal. Calc. for C 12 10 6 2 S (MW = 302.32): C 47.68, 3.33, 27.80, Found: C 47.59, 3.28, 27.71 %. 7-(2 -Thiazolyl)-6,8-diimino-2,5-pyrrolo[3,4-f][1,3,5]triazepine-2(1),4-(3,5)-dione (9). Yield 2.19 g (79 %), m.p. = 274 o C (ethanol); IR (KBr) ν/ cm -1 : 1688 (C), 3356 (), 3351 (C=), 1610 (C=), 1644 (C=C); 1 MR (CDCl 3 ) δ/ppm: 7.8, 7.4 (br, s, 3, ), 5.2 (s, 2, -C=) D 2 exchangeable, 3.2 (d, J = 3.4 z, 1, thiazole ring), 3.5(d, J = 3.7 z, 1, thiazole ring); 13 C MR (CDCl 3 ) δ: 134.8 (-C), 135.3 (-C), 136.4 (C), 137.2 (C), 139.5 (C), 143.7 (C), 144.4 (C), 163.4 (C), 164.5 (C); m/z: 277 (M +, 73 %). Anal. Calc. for C 9 7 7 2 S (MW = 277.27): C 38.99, 2.54, 35.36, Found: C 38.94, 2.48, 35.27 %. 6-Imino-(quinazolin-4-oxo-yl)[1,2 :7,8]-2,5-pyrrolo[3,4-f][1,3,5]triazepine 2(1),4(3,5)-dione (10). Yield 2.25 g (76 %), m.p. = 258 o C (dilute acetic acid); IR (KBr) ν/ cm -1 : 1687 (C), 3348 (), 3338 (C=), 1615 (C=), 1645 (C=C); 1 MR (CDCl 3 ) δ/ppm: 7.6, 7.3 (br, s, 3, ), 5.4 (s,, -C=) D 2 exchangeable, 7.68 (1, dd, J = 6.65, 6.65 z), 7.78 (1, dd, J = 7.7, 7.7 z), 7.84 (1, d, J = 7.5 z), 8.35 (1, d, J = 8.7 z); 13 C MR (CDCl 3 ) δ: 129.3 (-C), 130.4 (-C), 131.6 (-C), 132.4 (-C), 134.5 (C), 136.7 (C), 138.2 (C), 142.8 (C), 143.4 (C), 145.7 (C), 161.8, 162.2, 164.0 (3 x C); m/z: 296 (M +, 48 %). Anal. Calc. for C 13 8 6 3 (MW = 296.25): C 52.71, 2.72, 28.37, Found: C 52.64, 2.69, 28.29 %. 6-Imino-(quinazolin-4-imino-yl)[1,2 :7,8]-2,5-pyrrolo[3,4-f][1,3,5]triazepine- 2(1),4(3,5)- dione (11). Yield 2.39 g (81 %), m.p. = 261 o C (dilute acetic acid); IR (KBr) ν/ cm -1 : 1682 (C), 3360 (), 3350 (C=), 1615 (C=), 1644 (C=C); 1 MR (CDCl 3 ) δ/ppm: 7.7, 7.4 (br, s, 3, ), 5.0 (s, 2, 2x C=) D 2 exchangeable, 7.84 (1, dd, J = 6.30, 6.30 z), 7.66 (1, dd, J = 7.3, 7.3 z), 7.60 (1, d, J = 6.9 z), 8.34 (1, d, J = 8.5 z); 13 C MR (CDCl 3 ) δ: 129.8 (-C), 130.2 (-C), 131.7 (-C), 132.5 (-C), 134.5 (C), 136.7 (C), 138.2 (C), 142.7 (C), 143.4 (C), 144.2 (C), 145.8 (C), 161.7, 162.6 (2x C); m/z: 295 (M +, 79 %). Anal. Calc. for C 13 9 7 2 (MW = 295.26): C 52.88, 3.07, 33.21, Found: C 52.83, 3.01, 33.17 %. 6-Imino-(pyrido[2,3 :4,5]pyrimidine-6-one-yl)[2,3 :7,8]-2,5-pyrrolo[3,4- f][1,3,5]triazepine-2 (1),4-(3,5)-dione (12). Yield 2.52 g (85%), m.p. = 255 o C (dilute acetic acid); IR (KBr) ν/ cm -1 : 1685 (C), 3358 (), 3341 (C=), 1620 (C=), 1642 (C=C); 1 MR (CDCl 3 ) δ/ppm: 7.7, 7.3 (br, s, 3, ), 4.3 (s,, C=) D 2 exchangeable, 8.90 (dq, J = 5, 2 z, 1, pyridine ring), 7.25 (dd, J = 5, 7 z, 1, pyridine ring), 8.75 (dq, J = 7, 2 z, 1, pyridine ring); 13 C MR (CDCl 3 ) δ: 130.6 (-C), 131.6 (-C), 132.4 (-C), 134.5 (C), 136.7 (C), 138.2 (C), 142.8 (C), 143.4 (C), 145.7 (C), 161.8, 162.3, 164.2 (3 x C); m/z: 297 (M +, 49 %). Anal. Calc. for C 12 7 7 3 (MW = 297.23): C 48.49, 2.37, 32.99, Found: C 48.47, 2.32, 32.91 %. 6-Imino-(pteridin-4(1)-one-yl)[1,2 :7,8]-2,5-pyrrolo[3,4-f][1,3,5]triazepine- 2(1),4(3,5)- dione (13). Yield 2.29 g (77 %), m.p. = 246 o C (dilute acetic acid); IR (KBr) ISS 1424-6376 Page 76

General Papers ARKIVC 2004 (i) 71-78 ν/ cm -1 : 1685 (C), 3358 (), 3344 (C=), 1618 (C=), 1642 (C=C); 1 MR (CDCl 3 ) δ/ppm: 7.8, 7.2 (br, s, 3, ), 4.5 (s,, C=) D 2 exchangeable, 8.65 (d, J = 6.8 z, 1, pyrazine ring), 8.36 (d, J = 6.8 z, 1, pyrazine ring); 13 C MR (CDCl 3 ) δ: 131.5 (-C), 132.6 (-C), 134.5 (C), 136.7 (C), 138.2 (C), 142.8 (C), 143.4 (C), 145.4 (C), 161.6, 162.4, 164.1 (3 x C); m/z: 298 (M +, 33 %). Anal. Calc. for C 11 6 8 3 (MW = 298.22): C 44.30, 2.03, 37.57, Found: C 44.25, 1.98, 37.52 %. Preparation of 6,9-diamino-2,5-pyridazino[4,5-f][1,3,5]triazepine-2(1), 4-(3,5)-dione (14). Compound 4 (1.77 g, 0.01 mol) and hydrazine hydrate (0.01 mole) were refluxed in ethanol with triethylamine (0.5 ml) for 4 h. The solvent was then evaporated in vacuo and the remaining product was triturated with a little of water and then acidified with Cl acid. The resulting solid product was collected by filtration and crystallized from ethanol. 14: 1.52 g (73 %), m.p. = 264 o C (ethanol); IR (KBr) ν/ cm -1 : 1672 (C), 3352 (), 3248 ( 2 ), 1620 (C=), 1638 (C=C); 1 MR (CDCl 3 ) δ/ppm: 7.1, 7.3 (br, s, 3, ), 6.3 (s, 2, 2 ); 13 C MR (CDCl 3 ) δ: 140.6, 141.5, 142.3 (C), 143.8 (C), 161.8, 162.2 (2xC); m/z: 209 (M +, 66 %). Anal. Calc. for C 6 7 7 2 (MW = 209.17): C 34.45, 3.37, 46.87, Found: C 34.39, 3.32, 46.80 %. Preparation of diimidazolyl[3,4,5,3,4,5][e,f]pyridazino[4,5-f][1,3,5]triazepine-2,4-dione (15). A mixture of 14 (2.09 g, 0.01 mol), an equimolar amount of triethyl orthoformate and acetic anhydride (16 ml) was refluxed for 5 h. The solvent was removed under reduced pressure. The resulting solid product was crystallized from benzene/petroleum ether (1:1). 15: 1.74 g (71%), m.p. = 193 o C (benzene/petroleum); IR (KBr) ν/ cm -1 : 1675 (C), 3345 (), 1622 (C=), 1638 (C=C); 1 MR (CDCl 3 ) δ/ppm: 8.0 (br, s,, ) D 2 exchangeable, 8.15 (s, 1, C); 13 C MR (CDCl 3 ) δ: 136.2 (C), 137.4 (-C), 138.7 (C), 139.4 (C), 144.1 (C), 144.7 (C), 162.9, 163.2 (2 x C); m/z: 245 (M +, 76 %). Anal. Calc. for C 9 7 7 2 (MW = 245.20): C 44.09, 2.88, 39.99, Found: C 44.02, 2.83, 39.95 %. Preparation of 6,10-diamino-1,3,5,7,9-pentazaheptalin-2,4,8-trione, 16 and 6,10-diamino-8- thioxo-1,3,5,7,9-pentazaheptaline-2,4-dione (17). Compound 4 (1.77 g, 0.01 mol) and urea 5j or thiourea 5k (0.01 mole) were refluxed in ethanol (50 ml) containing triethylamine (0.5 ml) for 3 h. The mixture was then collected by filtration then recrystallized from ethanol. 16: 1.61 g (68 %), m.p. > 300 o C (ethanol); IR (KBr) ν/ cm -1 : 1683 (C), 3355 (), 3252 ( 2 ), 1620 (C=), 1642 (C=C); 1 MR (CDCl 3 ) δ/ppm: 7.7, 7.5 (br, s, 3, ), 6.8 (s, 2, 2 ); 13 C MR (CDCl 3 ) δ: 137.6 (C), 138.4 (C), 144.3 (C), 145.8 (C), 163.3, 163.5, 165.2 (3 x C); m/z: 237 (M +, 82 %). Anal. Calc. for C 7 7 7 3 (MW = 237.17): C 35.45, 2.97, 41.34, Found: C 35.37, 2.94, 41.29 %. 17: 1.87 g (74 %), m.p. = 286 o C (ethanol); IR (KBr) ν/ cm -1 : 1683 (C), 1195 (CS), 3354 (), 3250 ( 2 ), 1620 (C=), 1642 (C=C); 1 MR (CDCl 3 ) δ/ppm: 7.8, 7.3 (br, s, 3, ), 6.6 (s, 2, 2 ); 13 C MR (CDCl 3 ) δ: 139.6 (C), 140.4 (C), 144.3 (C), 145.8 (C), 163.8, 164.1 (2 x C), 181.4 (CS); m/z: 253 (M +, 82 %). Anal. Calc. for C 7 7 7 2 S (MW = 253.24): C 33.17, 2.78, 38.71, Found: C 33.09, 2.72, 38.66 %. Preparation of 3-hydro-2,4-dichloro-6,7-dicyano-1,3,5-triazepine (18). A mixture of 4 (1.77 g, 0.01 mole), phosphorus oxychloride (20 ml) and,-dimethylaniline (2 ml) was ISS 1424-6376 Page 77

General Papers ARKIVC 2004 (i) 71-78 refluxed for 3 h. After removal of the excess of phosphorus oxychloride, the residue was added 200 ml of ice water. The precipitate was collected by filtration and recrystallized from chloroform. 18: 1.64 g (77 %), m.p. = 183 o C (chloroform); IR (KBr) ν/ cm -1 : 2230 (C), 698 (C Cl), 1660 (C=C); 1 MR (CDCl 3 ) δ/ppm: 7.2 (br, s,, ) D 2 exchangeable; 13 C MR (CDCl 3 ) δ: 117.6, 117.8 (2 x C), 141.2 (C), 141.6 (C), 144.3 (C), 145.8 (C); m/z: 214 (M +, 12 %). Anal. Calc. for C 6 5 Cl 2 (MW = 214.01): C 33.67, 0.47, 32.72, Found: C 33.58, 0.42, 32.65 %. References 1. Mague, J. T.; Eduok, E. E. J. Chem. Crystallogr. 2000, 30, 311. 2. Booth, B. L.; Dias, A. M.; Proenca, M. F.; Zaki, M. E. A. J. rg. Chem. 2001, 66, 8436. 3. gura,.; Takahashi,.; Takeda, K. Chem. Pharm. Bull. 1981, 7, 1832. 4. Butler, A. R.; ussain, I. J. Chem. Soc., Perkin Trans. 2 1981, 317. 5. Shanzer, A. Angew. Chem. 1980, 92, 325. 6. Yu, Y.; strech, J. M.; oughten, R. A. rg. Lett. 2001, 3, 2797. 7. Alves, M. J.; Al-Duaij,. K.; Booth, B. L.; Carvalho, M. A.; Eastwood, P. R.; Proenca, M. F. J. R. P. J. Chem. Soc., Perkin Trans. 1 1994, 3571. 8. Alves, M. J.; Carvalho, M. A.; Proenca, M. F. J. R. P.; Booth, B. L. J. eterocycl. Chem. 2000, 37, 1041. 9. Bunnenberg, R.; Jochims, J. C. Chem. Ber. 1981, 114, 2064. 10. Elgemeie, G..; El-Ezbawy, S. R.; Ali,. A. Synth. Commun. 2001, 31, 3459. 11. Vovk, M. V. Chem. eterocycl. Compd. (Engl. Transl.) 1993, 29, 972. 12. Abdel-Razik,.. J. Chin. Chem. Soc. 2003, 50, 887. ISS 1424-6376 Page 78

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