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The reaction of phthalonitriles <jats:bold>1<\/jats:bold>, <jats:bold>2<\/jats:bold>, or <jats:bold>4<\/jats:bold> (R<jats:sup>1<\/jats:sup>, R<jats:sup>3<\/jats:sup>, R<jats:sup>4<\/jats:sup>=H, R<jats:sup>2<\/jats:sup>=NO<jats:sub>2<\/jats:sub>) (4\u2005equivs.) with Et<jats:sub>2<\/jats:sub>NOH (8\u2005equivs.) in the presence of a metal salt MCl<jats:sub>2<\/jats:sub> (M=Zn, Cd, Co, Ni) (1\u2005equiv.) in <jats:italic>n\u2010<\/jats:italic>BuOH or without solvent results in the formation of metallated phthalocyanine species (<jats:bold>9<\/jats:bold>\u2013<jats:bold>17<\/jats:bold>). Upon refluxing in freshly distilled dry <jats:italic>chloroform<\/jats:italic>, phthalonitrile <jats:bold>1<\/jats:bold> or its substituted analogues <jats:bold>2<\/jats:bold>, <jats:bold>3<\/jats:bold> or <jats:bold>5<\/jats:bold> (R<jats:sup>1<\/jats:sup>\u2013R<jats:sup>4<\/jats:sup>=F) (1\u2005equiv.) react with <jats:italic>N<\/jats:italic>,<jats:italic>N<\/jats:italic>\u2010diethylhydroxylamine (2\u2005equivs.) affording 3\u2010iminoisoindolin\u20101\u2010ones <jats:bold>18<\/jats:bold>\u2013<jats:bold>21<\/jats:bold> (<jats:bold>Route B<\/jats:bold>) isolated in good yields (55\u201380\u2009%). All the prepared compounds were characterized with C, H, and N elemental analyses, ESI\u2010MS, IR, and compounds <jats:bold>18<\/jats:bold>\u2013<jats:bold>21<\/jats:bold> also by 1D (<jats:sup>1<\/jats:sup>H, <jats:sup>13<\/jats:sup>C{<jats:sup>1<\/jats:sup>H}), and 2D (<jats:sup>1<\/jats:sup>H,<jats:sup>15<\/jats:sup>N\u2010HMBC and <jats:sup>1<\/jats:sup>H,<jats:sup>13<\/jats:sup>C\u2010HMQC, <jats:sup>1<\/jats:sup>H,<jats:sup>13<\/jats:sup>C\u2010HMBC) NMR spectroscopy.<\/jats:p>","DOI":"10.1002\/adsc.200700261","type":"journal-article","created":{"date-parts":[[2007,12,14]],"date-time":"2007-12-14T08:47:01Z","timestamp":1197622021000},"page":"135-142","source":"Crossref","is-referenced-by-count":36,"title":["Novel and Mild Route to Phthalocyanines and 3\u2010Iminoisoindolin\u20101\u2010ones <i>via N<\/i>,<i>N<\/i>\u2010Diethylhydroxylamine\u2010Promoted Conversion of Phthalonitriles and a Dramatic Solvent\u2010Dependence of the Reaction"],"prefix":"10.1002","volume":"350","author":[{"given":"Konstantin\u2005V.","family":"Luzyanin","sequence":"first","affiliation":[]},{"given":"Vadim Yu.","family":"Kukushkin","sequence":"additional","affiliation":[]},{"given":"Maximilian N.","family":"Kopylovich","sequence":"additional","affiliation":[]},{"given":"Alexey A.","family":"Nazarov","sequence":"additional","affiliation":[]},{"given":"Mathea Sophia","family":"Galanski","sequence":"additional","affiliation":[]},{"given":"Armando J.\u2005L.","family":"Pombeiro","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2008,1,8]]},"reference":[{"key":"e_1_2_1_1_2","first-page":"1","volume-title":"Phthalocyanines, in: Comprehensive Coordination Chemistry","author":"McKeown N. 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