ON THE QUESTION OF SELECTIVE PROTOCOL FOR THE PREPARATION OF JUGLONE <i>via</i> (4+2) CYCLOADDITION INVOLVING 3-HYDROXYPYRIDAZINE: DFT MECHANISTIC STUDY

Авторы

  • Radomir Jasiński Department of Organic Chemistry and Technology, Cracow University of Technology, 24 Warszawska St., Cracow 31-155, Poland

DOI:

https://doi.org/10.1007/7034

Ключевые слова:

3-hydroxypyridazine, juglone, (4 2) cycloaddition, mechanism, molecular electron density theory.

Аннотация

The possibility of preparation of juglone via Diels–Alder reaction of 3-hydroxypyridazine and 2-nitroquinone was analyzed on the basis of DFT computational study. It was found that key stage of the proposed transformation is head-to-head, polar cycloaddition process, which is realized without formation of zwitterionic intermediate. Further transformations of the intermediate exhibit nature of pseudocyclic reactions with nonconcerted reorganization of the electron density.

Опубликован

2023-04-11

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