Unknown

Dataset Information

0

Three-Component Coupling of Aldehydes, 2-Aminopyridines, and Diazo Esters via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrido[1,2- a]pyrimidin-4-ones.

ABSTRACT: Imines formed in situ from 2-aminopyridines and aldehydes undergo Rh(III)-catalyzed imidoyl C-H activation and coupling with diazo esters to give pyrido[1,2- a]pyrimidin-4-ones. Aromatic and enolizable aliphatic aldehydes were both effective substrates, and a broad range of functional groups were incorporated at different sites on the heterocyclic products. In addition, methoxy and dimethylamino functionalities could be directly installed on the pyrimidine ring by employing trimethyl orthoformate or N, N-dimethylformamide dimethyl acetal in place of the aldehyde, respectively.

SUBMITTER: Hoang GL 

PROVIDER: S-EPMC6561808 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Three-Component Coupling of Aldehydes, 2-Aminopyridines, and Diazo Esters via Rhodium(III)-Catalyzed Imidoyl C-H Activation: Synthesis of Pyrido[1,2- a]pyrimidin-4-ones.

Hoang Gia L GL   Zoll Adam J AJ   Ellman Jonathan A JA  

Organic letters 20190321 11

Imines formed in situ from 2-aminopyridines and aldehydes undergo Rh(III)-catalyzed imidoyl C-H activation and coupling with diazo esters to give pyrido[1,2- a]pyrimidin-4-ones. Aromatic and enolizable aliphatic aldehydes were both effective substrates, and a broad range of functional groups were incorporated at different sites on the heterocyclic products. In addition, methoxy and dimethylamino functionalities could be directly installed on the pyrimidine ring by employing trimethyl orthoformat  ...[more]

Similar Datasets

Unknown Electro-Oxidative C3-Selenylation of Pyrido[1,2-<i>a</i>]pyrimidin-4-ones.
| S-EPMC10005275 | biostudies-literature
Unknown Hexafluoroisopropyl alcohol mediated synthesis of 2,3-dihydro-4H-pyrido[1,2-a]pyrimidin-4-ones.
| S-EPMC5090868 | biostudies-literature
Unknown Hexafluoroisopropanol mediated benign synthesis of 2H-pyrido[1,2-a]pyrimidin-2-ones by using a domino protocol.
| S-EPMC5800427 | biostudies-literature
Unknown Pyridine group assisted addition of diazo-compounds to imines in the 3-CC reaction of 2-aminopyridines, aldehydes, and diazo-compounds.
| S-EPMC3632368 | biostudies-literature
Unknown 3-(2-Chloro-ethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one.
| S-EPMC2977208 | biostudies-literature
Unknown CuI-catalyzed synthesis of multisubstituted pyrido[1,2-<i>a</i>]pyrimidin-4-ones through tandem Ullmann-type C-N cross-coupling and intramolecular amidation reaction.
| S-EPMC10424054 | biostudies-literature
Unknown Spiro-[cyclo-pentane-1,2'(1'H)-pyrido[2,3-d]pyrimidin]-4'(3'H)-one.
| S-EPMC3008029 | biostudies-literature
Unknown [CMMIM][BF4–] Ionic Liquid-Catalyzed Facile, One-Pot Synthesis of Chromeno[4,3-d]pyrido[1,2-a]pyrimidin-6-ones: Evaluation of Their Photophysical Properties and Theoretical Calculations
| S-EPMC9631728 | biostudies-literature
Unknown Aqua-bis(2,3-dimethyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-olato)nickel(II).
| S-EPMC2980000 | biostudies-literature
Unknown 6'-Bromo-1'H-spiro-[cyclo-hexane-1,2'-pyrido[2,3-d]pyrimidin]-4'(3'H)-one.
| S-EPMC3254517 | biostudies-literature