Reaction cascades initiated by nucleophilic attack of heteropentalene mesomeric betaine and nitrogen-rich mesoionic tetrazolium-5-amides on electron-deficient unsaturated compounds. Synthesis of novel heterocyclic systems |
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Authors: | Araki Shuki Kuzuya Masashi Hamada Kenji Nogura Masatoshi Ohata Nayumi |
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Institution: | Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan. araki@ach.nitech.ac.jp |
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Abstract: | The reactions of heteropentalene mesomeric betaine 1 and nitrogen-rich mesoionic tetrazolium-5-amides 4, 11 and 16-18 with electron-deficient unsaturated compounds have been studied. Novel heterocyclic systems, tetrazolo4,5-a]1,7]benzodiazonine inner salt 2 and 3-oxo-3,7-dihydro-2H-pyrazolo3,4-b]pyridine 5, have been synthesized by the reactions of dimethyl acetylenedicarboxylate with 1 and tetrazolium-5-anilide 4, respectively, and fully characterized by X-ray crystallography. It has been found that the reactions of other tetrazolium-5-amides are also initiated by the nucleophilic addition of the electron-rich amide nitrogen to the electron-deficient unsaturated compounds. |
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