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Iridium/graphene nanostructured catalyst for the N-alkylation of amines to synthesize nitrogen-containing derivatives and heterocyclic compounds in a green process.

ABSTRACT: A facile iridium/graphene-catalyzed methodology providing an efficient synthetic route for C-N bond formation is reported. This catalyst can directly promote the formation of C-N bonds, without pre-activation steps, and without solvents, alkalis and other additives. This protocol provides a direct N-alkylation of amines using a variety of primary and secondary alcohols with good selectivity and excellent yields. Charmingly, the use of diols resulted in intermolecular cyclization of amines, and such products are privileged structures in biologically active compounds. Two examples illustrate the advantages of this catalyst in organic synthesis: the tandem catalysis to synthesize hydroxyzine, and the intermolecular cyclization to synthesize cyclizine. Water is the only by-product, which makes this catalytic process sustainable and environmentally friendly.

SUBMITTER: Chen TR

PROVIDER: S-EPMC8981502 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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Iridium/graphene nanostructured catalyst for the <i>N</i>-alkylation of amines to synthesize nitrogen-containing derivatives and heterocyclic compounds in a green process.

Chen Tsun-Ren TR Chen Yu-Tung YT Chen Yi-Sheng YS Lee Wen-Jen WJ Lin Yen-Hsing YH Wang Hao-Chen HC

RSC advances 20220209 8

A facile iridium/graphene-catalyzed methodology providing an efficient synthetic route for C-N bond formation is reported. This catalyst can directly promote the formation of C-N bonds, without pre-activation steps, and without solvents, alkalis and other additives. This protocol provides a direct <i>N</i>-alkylation of amines using a variety of primary and secondary alcohols with good selectivity and excellent yields. Charmingly, the use of diols resulted in intermolecular cyclization of amines ...[more]

PMID: 35425512

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Project description:2-Amino-9H-pyrido[2,3-b]indole (AαC) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) are carcinogenic heterocyclic aromatic amines (HAA) that arise during the burning of tobacco and cooking of meats. UDP-glucuronosyltransferases (UGT) detoxicate many procarcinogens and their metabolites. The genotoxic N-hydroxylated metabolite of AαC, 2-hydroxyamino-9H-pyrido[2,3-b]indole (HONH-AαC), undergoes glucuronidation to form the isomeric glucuronide (Gluc) conjugates N(2)-(β-d-glucosidurony1)-2-hydroxyamino-9H-pyrido[2,3-b]indole (AαC-HON(2)-Gluc) and O-(β-d-glucosidurony1)-2-hydroxyamino-9H-pyrido[2,3-b]indole (AαC-HN(2)-O-Gluc). AαC-HON(2)-Gluc is a stable metabolite but AαC-HN(2)-O-Gluc is a biologically reactive intermediate, which covalently adducts to DNA at levels that are 20-fold higher than HONH-AαC. We measured the rates of formation of AαC-HON(2)-Gluc and AαC-HN(2)-O-Gluc in human organs: highest activity occurred with liver and kidney microsomes, and lesser activity was found with colon and rectum microsomes. AαC-HN(2)-O-Gluc formation was largely diminished in liver and kidney microsomes, by niflumic acid, a selective inhibitor UGT1A9. In contrast, AαC-HON(2)-Gluc formation was less affected and other UGT contribute to N(2)-glucuronidation of HONH-AαC. UGT were reported to catalyze the formation of isomeric Gluc conjugates at the N(2) and N3 atoms of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine (HONH-PhIP), the genotoxic metabolite of PhIP. However, we found that the N3-Gluc of HONH-PhIP also covalently bound to DNA at higher levels than HONH-PhIP. The product ion spectra of this Gluc conjugate acquired by ion trap mass spectrometry revealed that the Gluc moiety was linked to the oxygen atom of HONH-PhIP and not the N3 imidazole atom of the oxime tautomer of HONH-PhIP as was originally proposed. UGT1A9, an abundant UGT isoform expressed in human liver and kidney, preferentially forms the O-linked Gluc conjugates of HONH-AαC and HONH-PhIP as opposed to their detoxicated N(2)-Gluc isomers. The regioselective O-glucuronidation of HONH-AαC and HONH-PhIP, by UGT1A9, is a mechanism of bioactivation of these ubiquitous HAAs.

Dataset Information

Iridium/graphene nanostructured catalyst for the N-alkylation of amines to synthesize nitrogen-containing derivatives and heterocyclic compounds in a green process.

Publications

Iridium/graphene nanostructured catalyst for the <i>N</i>-alkylation of amines to synthesize nitrogen-containing derivatives and heterocyclic compounds in a green process.

Similar Datasets

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