New type of tetrazine‐substituted metallophthalocyanines by microwave irradiation: Synthesis and characterization

5,6‐bis(4‐methylphenyl)‐2,3‐dihydro‐1,2,3,4‐tetrazine 2 was synthesized by the dimerization of ethyl p‐methylbenzoateformylhydrazone 1 in hydrazinehydrate solution. 2,3‐bis(4‐methylphenyl)‐6,7,14,15‐tetrahydro1,2,3,4]tetrazino 2,3d]1,8, 4,5]benzodithia‐diazecine‐10,11‐dicarbonitrile 4 was sythesized by cyclization reaction of tetrazine monomer 2 onto 1,2‐bis‐(2‐iodoethylmercapto)‐4,5‐dicyanobenzene 3 . Co(II) and Cu(II) phthalocyanine complexes were prepared by reaction of the dinitrile compound ( 4 ) with the chlorides of Co(II), Cu(II), and DMAE at 175°C, 350 W in a microwave oven for 10 min. Zn(II)‐phthalocyanine complex was prepared by reaction of the dinitrile compound 4 with the acetate of Zn(II) and DMAE at 175°C, 350 W in a microwave oven for 10 min. The new compounds were characterized by a combination of IR, ¹H‐NMR, ¹³C? NMR, UV‐vis, elemental analysis, and MS spectral data. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:456–461, 2010; View this article online at wileyonlinelibrary.com . DOI 10.1002/hc.20623