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Denitrogenative dismantling of heteroaromatics by nucleophilic substitution reactions with diazomethyl compounds.

ABSTRACT: 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.

SUBMITTER: Biswas S

PROVIDER: S-EPMC11253183 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature

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Denitrogenative dismantling of heteroaromatics by nucleophilic substitution reactions with diazomethyl compounds.

Biswas Soumen S Empel Claire C Sanchez-Palestino Luis Mario LM Arman Hadi H Koenigs Rene M RM Doyle Michael P MP

Chemical science 20240617 28

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 sp<sup>2</sup>-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 ...[more]

PMID: 39027303

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