SNH reactions of pyrazine N-oxides and 1,2,4-triazine 4-oxides with CH-active compounds View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2003-07

AUTHORS

D. N. Kozhevnikov, I. S. Kovalev, A. M. Prokhorov, V. L. Rusinov, O. N. Chupakhin

ABSTRACT

Nucleophilic substitution of hydrogen in pyrazine N-oxides under the action of CH-active compounds requires activation with acylating agents. This activation facilitates aromatization of intermediate σH adducts via elimination of the acid residue to form substituted pyrazines. More electrophilic 1,2,4-triazine 4-oxides react with carbanions derived from CH-active compounds without additional activation according to a scheme, which has previously been unknown for azine N-oxides. This scheme involves aromatization of σH adducts through elimination of water by the E1cb mechanism. The reaction products occur in DMSO-d6 solutions predominantly as 6-methylene-1,6-dihydropyrazines and 5-methylene-4,5-dihydro-1,2,4-triazines. More... »

PAGES

1588-1594

Identifiers

URI

http://scigraph.springernature.com/pub.10.1023/a:1025601311393

DOI

http://dx.doi.org/10.1023/a:1025601311393

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1025643990


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