{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,15]],"date-time":"2025-10-15T17:20:05Z","timestamp":1760548805641},"reference-count":10,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2009,3,11]],"date-time":"2009-03-11T00:00:00Z","timestamp":1236729600000},"content-version":"vor","delay-in-days":5489,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Journal of Heterocyclic Chem"],"published-print":{"date-parts":[[1994,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>(<jats:italic>Z<\/jats:italic>)\u2010<jats:italic>N<\/jats:italic>\u2010(2\u2010amino\u20101,2\u2010dicyanovinyl)\u2010<jats:italic>N'<\/jats:italic>\u2010benzylformamidine <jats:bold>6<\/jats:bold> has been prepared both from the reaction of benzylisonitrile with the hydrochloride salt of diaminomaleonitrile and from reaction of ethyl (<jats:italic>Z<\/jats:italic>)\u2010<jats:italic>N<\/jats:italic>\u2010(2\u2010amino\u20101,2\u2010dicyanovinyl)formimidate with benzylamine. Based\u2010catalyzed cyclization of amidine <jats:bold>6<\/jats:bold> led to imidazoles <jats:bold>7<\/jats:bold> and <jats:bold>8<\/jats:bold> depending on the reaction conditions. Compound <jats:bold>7<\/jats:bold> reacts with acetone and butane\u20102,3\u2010dione to give the 2,2\u2010disubstituted\u20106\u2010carbamoyl\u20101,2\u2010dihydropurines <jats:bold>9a<\/jats:bold> and <jats:bold>9b<\/jats:bold> respectively. 2\u2010Methyl\u20106\u2010carbamoylpurine <jats:bold>12<\/jats:bold> was obtained from the reaction of imidazole <jats:bold>7<\/jats:bold> with pentane\u20102,4\u2010dione. The same compound was observed in the <jats:sup>1<\/jats:sup>H nmr spectrum of a solution of 1,2\u2010dihydropurine <jats:bold>9b<\/jats:bold> in deuteriochloro\u2010form. Benzylimidazole <jats:bold>7<\/jats:bold> can be acetylated with acetic anhydride leading to compound <jats:bold>14<\/jats:bold>. This, in solution, undergoes an acyl migration reaction to give imidazoles <jats:bold>15<\/jats:bold> and <jats:bold>17<\/jats:bold>. Imidazole <jats:bold>15<\/jats:bold> cyclizes in the presence of base to the corresponding 6\u2010cyanopurine <jats:bold>16<\/jats:bold>. A solution of <jats:bold>14<\/jats:bold> in methanol is slowly converted into the 6\u2010methoxypurine <jats:bold>18<\/jats:bold>, possibly <jats:italic>via<\/jats:italic> a methoxymidoyl intermediate. A similar intermediate <jats:bold>13<\/jats:bold> has been isolated from <jats:bold>7<\/jats:bold> in methanol.<\/jats:p>","DOI":"10.1002\/jhet.5570310215","type":"journal-article","created":{"date-parts":[[2009,3,11]],"date-time":"2009-03-11T11:30:43Z","timestamp":1236771043000},"page":"345-350","source":"Crossref","is-referenced-by-count":23,"title":["Synthesis of 4\u2010 and 5\u2010disubstituted 1\u2010benzylimidazoles, important precursors of purine analogs"],"prefix":"10.1002","volume":"31","author":[{"given":"M. Jos\u00e9","family":"Alves","sequence":"first","affiliation":[]},{"given":"M. Fernanda J. R. P.","family":"Proen\u00e7a","sequence":"additional","affiliation":[]},{"given":"Brian L.","family":"Booth","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2009,3,11]]},"reference":[{"key":"e_1_2_1_2_2","doi-asserted-by":"crossref","unstructured":"B. L.Booth R. D.CosterandM. F.Proen\u00e7a J. Chem. Soc. Perkin Trans. 1 1521(1987).","DOI":"10.1039\/P19870001521"},{"key":"e_1_2_1_3_2","unstructured":"M. J.Alves B. L.BoothandM. F.Proen\u00e7a J. Chem. Soc. Perkin Trans. 1 1705(1990)."},{"key":"e_1_2_1_4_2","unstructured":"M. J.Alves B. L.Booth A. P.FreitasandM. F.Proen\u00e7a J. Chem. Soc. Perkin Trans. 1 913(1992)."},{"key":"e_1_2_1_5_2","doi-asserted-by":"crossref","unstructured":"B. L.Booth A. M.DiasandM. F.Proen\u00e7a J. Chem. Soc. 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