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

文献情報

出版日 2003-02-14

DOI 10.1039/B211000H

インパクトファクター 3.876

著者

Shuki Araki, Masashi Kuzuya, Kenji Hamada, Masatoshi Nogura, Nayumi Ohata

原文を見る

要旨

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, tetrazolo[4,5-a][1,7]benzodiazonine inner salt 2 and 3-oxo-3,7-dihydro-2H-pyrazolo[3,4-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.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

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