Unknown

Dataset Information

0

Regioselective Pd-catalyzed direct C1- and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-ij]quinoline derivatives.

ABSTRACT: The Pd-catalyzed C-H bond functionalization of lilolidine was investigated. The use of a palladium-diphosphine catalyst associated to acetate bases in DMA was found to promote the regioselective arylation at ?-position of the nitrogen atom of lilolidine with a wide variety of aryl bromides. From these ?-arylated lilolidines, a second arylation at the ?-position gives the access to ?,?-diarylated lilolidines containing two different aryl groups. The one pot access to ?,?-diarylated lilolidines with two identical aryl groups is also possible by using a larger amount of aryl bromide. The synthesis of 5,6-dihydrodibenzo[a,c]pyrido[3,2,1-jk]carbazoles from lilolidine via three successive direct arylations is also described. Therefore, this methodology provides a straightforward access to several lilolidine derivatives from commercially available compounds via one, two or three C-H bond functionalization steps allowing to tune their biological properties.

SUBMITTER: Huang HY 

PROVIDER: S-EPMC6719733 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Regioselective Pd-catalyzed direct C1- and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-<i>ij</i>]quinoline derivatives.

Huang Hai-Yun HY   Li Haoran H   Roisnel Thierry T   Soulé Jean-François JF   Doucet Henri H  

Beilstein journal of organic chemistry 20190829

The Pd-catalyzed C-H bond functionalization of lilolidine was investigated. The use of a palladium-diphosphine catalyst associated to acetate bases in DMA was found to promote the regioselective arylation at α-position of the nitrogen atom of lilolidine with a wide variety of aryl bromides. From these α-arylated lilolidines, a second arylation at the β-position gives the access to α,β-diarylated lilolidines containing two different aryl groups. The one pot access to α,β-diarylated lilolidines wi  ...[more]

Similar Datasets

Unknown Methyl 4-methyl-2-oxo-1,2,5,6-tetra-hydro-4H-pyrrolo[3,2,1-ij]quinoline-6-carboxyl-ate.
| S-EPMC2977288 | biostudies-literature
Unknown Crystal structure and DFT study of 8-hy-droxy-1,2,3,5,6,7-hexa-hydro-pyrido[3,2,1-ij]quinoline-9-carbaldehyde.
| S-EPMC5418808 | biostudies-literature
Unknown 6-Hy-droxy-1,2-dihydro-4H-pyrrolo-[3,2,1-ij]quinolin-4-one.
| S-EPMC3588512 | biostudies-literature
Unknown Novel 2,3-Dihydro-1H-pyrrolo[3,2,1-ij]quinazolin-1-ones: Synthesis and Biological Evaluation.
| S-EPMC6155753 | biostudies-literature
Unknown Deoxygenative C2-heteroarylation of quinoline <i>N</i>-oxides: facile access to α-triazolylquinolines.
| S-EPMC7934756 | biostudies-literature
Unknown 7-Pivaloyl-5,6-dihydro-4H-naphtho[3,2,1-de]isoquinoline-4,6-dione.
| S-EPMC2984060 | biostudies-literature
Unknown 6-Eth-oxy-carbonyl-5,7-dihy-droxy-2,3-dihydro-1H-pyrido[3,2,1-ij]quinolinium tribromide.
| S-EPMC3588293 | biostudies-other
Unknown Multicomponent Reaction for the Synthesis of 5,6-Dihydropyrrolo[2,1-<i>a</i>]isoquinolines.
| S-EPMC6906948 | biostudies-literature
Unknown Synthesis of Gentamicins C1, C2, and C2a and Antiribosomal and Antibacterial Activity of Gentamicins B1, C1, C1a, C2, C2a, C2b, and X2.
| S-EPMC10425985 | biostudies-literature
Unknown 8-{(E)-[(4-Chloro-phen-yl)imino]-meth-yl}-1,1,7,7-tetra-methyl-1,2,3,5,6,7-hexa-hydro-pyrido[3,2,1-ij]quinolin-9-ol.
| S-EPMC3685040 | biostudies-literature