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Reaction of 2,3-diaminomaleonitrile with diones |
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| Authors: | Yasuhiro Kubota Toshihiro Shibata Jun Uehara Shinya Matsumoto Masaki Matsui |
| Institution: | a Department of Materials Science and Technology, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan b Faculty of Education and Human Sciences, Yokohama National University, Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan c Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan |
| Abstract: | 2,3-Diaminomaleonitrile (DAMN) was allowed to react with 2,6-heptanedione to produce (2Z)-2-amino-3-(1E)-3-methylcyclohex-2-enylideneamino]but-2-enedinitrile and (2Z)-2-amino-3-(1Z)-3-methylcyclohex-2-enylideneamino]but-2-enedinitrile. The reaction of DAMN with 2,7-octanedione yielded trans-5,8a-dimethyl-1,5a,6,7,8,8a-hexahydrocyclopentae]-1,4-diazepine-2,3-dicarbonitrile. DAMN reacted with 2,8-nonanedione to afford trans- and cis-5,9a-dimethyl-5a,6,7,8,9,9a-hexahydro-1H-benzoe]-1,4-diazepine-2,3-dicarbonitrile. These compounds were characterized by X-ray crystallography, NMR spectroscopy, and DFT calculations. |
| Keywords: | DAMN Diazepine Heterocycles DFT calculations Crystal structures Reaction mechanism |
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