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Denitrogenative dismantling of heteroaromatics by nucleophilic substitution reactions with diazomethyl compounds

Title data

Biswas, Soumen ; Empel, Claire ; Sanchez-Palestino, Luis Mario ; Arman, Hadi ; Koenigs, Rene M. ; Doyle, Michael P.:
Denitrogenative dismantling of heteroaromatics by nucleophilic substitution reactions with diazomethyl compounds.
In: Chemical Science. Vol. 15 (2024) . - pp. 11065-11071.
ISSN 2041-6539
DOI: https://doi.org/10.1039/D4SC01578A

Abstract in another language

Nucleophiles from deprotonation of diazomethyl compounds having diverse electron withdrawing groups react with 4-carboxylato-1,2,3-triazines at the 6-position to extrude dinitrogen and produce diazovinylketoesters compounds with five or six linear contiguous sp2-hybridized carbons, whereas these same nucleophiles react with 4-carboxylato-1,2,3-triazine 1-oxides, also at the 6-position, to form pyrazolines with the expulsion of nitrous oxide and cyanocarboxylate. This disparity is due to the significant difference in reactivity of the nucleophilic addition products.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 28 Mar 2025 08:58
Last Modified: 28 Mar 2025 08:58
URI: https://eref.uni-bayreuth.de/id/eprint/93027