Browse
Submit Data
Databases
API
Help

Dataset Information

23 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Facile Synthesis of Dihydroquinolines via Palladium Catalyzed Sequential Amination and Cyclisation of Morita-Baylis-Hillman Alcohols.

ABSTRACT: Quinolines and its derivatives are significant class of heterocyclic compounds which are identified as the key component in many natural products and biologically important molecules. We describe herein a facile method for the synthesis of quinoline derivatives from Morita-Baylis-Hillman (MBH) Alcohols via Palladium Catalyzed intramolecular aryl amination followed by allylic amination pathway. The reaction between a series of MBH alcohols and amino compounds (Tosyl, aliphatic and aromatic amines) under optimized reaction conditions with Pd(PPh₃)₂Cl₂/DPPP catalyst system, afforded the corresponding 1,2-dihydroquinolines upto 95?% isolated yield.

SUBMITTER: Sruthi PR

PROVIDER: S-EPMC7753362 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Facile Synthesis of Dihydroquinolines via Palladium Catalyzed Sequential Amination and Cyclisation of Morita-Baylis-Hillman Alcohols.

Sruthi Pambingal Rajan PR Sankar P Uma PU Saranya Thachora Venu TV Anas Saithalavi S

ChemistrySelect 20201118 43

Quinolines and its derivatives are significant class of heterocyclic compounds which are identified as the key component in many natural products and biologically important molecules. We describe herein a facile method for the synthesis of quinoline derivatives from Morita-Baylis-Hillman (MBH) Alcohols <i>via</i> Palladium Catalyzed intramolecular aryl amination followed by allylic amination pathway. The reaction between a series of MBH alcohols and amino compounds (Tosyl, aliphatic and aromatic ...[more]

PMID: 33363255

Similar Datasets

Dihydroquinolines, Dihydronaphthyridines and Quinolones by Domino Reactions of Morita-Baylis-Hillman Acetates.

Project description:An efficient synthetic route to highly substituted dihydroquinolines and dihydronaphthyridines has been developed using a domino reaction of Morita-Baylis-Hillman (MBH) acetates with primary aliphatic and aromatic amines in DMF at 50-90 °C. The MBH substrates incorporate a side chain acetate positioned adjacent to an acrylate or acrylonitrile aza-Michael acceptor as well as an aromatic ring activated toward SNAr ring closure. A control experiment established that the initial reaction was an SN2'-type displacement of the side chain acetate by the amine to generate the alkene product with the added nitrogen nucleophile positioned trans to the SNAr aromatic ring acceptor. Thus, equilibration of the initial alkene geometry is required prior to cyclization. A further double bond migration was observed for several reactions targeting dihydronaphthyridines from substrates with a side chain acrylonitrile moiety. MBH acetates incorporating a 2,5-difluorophenyl moiety were found to have dual reactivity in these annulations. In the absence of O2, the expected dihydroquinolines were formed, while in the presence of O2, quinolones were produced. All of the products were isolated in good to excellent yields (72-93%). Numerous cases (42) are reported, and mechanisms are discussed.

| S-EPMC7914960 | biostudies-literature

Organocatalytic asymmetric allylic amination of Morita-Baylis-Hillman carbonates of isatins.

Project description:The investigation of a Lewis base catalyzed asymmetric allylic amination of Morita-Baylis-Hillman carbonates derived from isatins afforded an electrophilic pathway to access multifunctional oxindoles bearing a C3-quaternary stereocenter, provided with good to excellent enantioselectivity (up to 94% ee) and in high yields (up to 97%).

| S-EPMC3458744 | biostudies-literature

Et<sub>3</sub>B-mediated and palladium-catalyzed direct allylation of ?-dicarbonyl compounds with Morita-Baylis-Hillman alcohols.

Project description:A practical and efficient palladium-catalyzed direct allylation of ?-dicarbonyl compounds with both cyclic and acyclic Morita-Baylis-Hillman (MBH) alcohols, using Et3B as a Lewis acid promoter, is described herein. A wide range of the corresponding functionalized allylated derivatives have been obtained in good yields and with high selectivity.

| S-EPMC5238553 | biostudies-literature

A facile and mild synthesis of trisubstituted allylic sulfones from Morita-Baylis-Hillman carbonates.

Project description:An efficient and catalyst-free synthesis of trisubstituted allylic sulfones through an allylic sulfonylation reaction of Morita-Baylis-Hillman (MBH) carbonates with sodium sulfinates has been developed. Under the optimized reaction conditions, a series of trisubstituted allylic sulfones were rapidly prepared in good to excellent yields (71%-99%) with good to high selectivity (Z/E from 79:21 to >99:1). Compared with known synthetic methods, the current protocol features mild reaction temperature, high efficiency and easily available reagents.

| S-EPMC6272667 | biostudies-other

Regioselective SN2' Mitsunobu reaction of Morita-Baylis-Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives.

Project description:A highly regioselective SN2' Mitsunobu reaction between Morita-Baylis-Hillman (MBH) alcohols, azodicarboxylates, and triphenylphosphine is developed, which provides an easy access to α-alkylidene-β-hydrazino acid derivatives in high yields and good stereoselectivity. This reaction represents the first direct transformation of MBH alcohols into hydrazines.

| S-EPMC4077529 | biostudies-literature

First DMAP-mediated direct conversion of Morita-Baylis-Hillman alcohols into ?-ketoallylphosphonates: Synthesis of ?-aminoallylphosphonates.

Project description:An efficient synthesis of a series of ?-ketoallylphosphonates through a direct conversion of both primary and secondary Morita-Baylis-Hillman (MBH) alcohols by trialkyl phosphites with or without DMAP, used as additive, and under solvent-free conditions, is described herein for the first time. Subsequently, a highly regioselective Luche reduction of the primary phosphonate 2a (R = H) gave the corresponding ?-hydroxyallylphosphonate 5 that further reacted with tosylamines in the presence of diiodine (15 mol %) as a catalyst, affording the corresponding SN2-type products 6a-d in 63 to 70% isolated yields. Alternatively, the alcohol 5 produced the corresponding acetate 7 which, mediated by Ce(III), was successfully converted into the corresponding ?-aminoallylphosphonates 8a-d.

| S-EPMC5238584 | biostudies-literature

Regioconvergent Nucleophilic Substitutions with Morita-Baylis-Hillman Fluorides.

Project description:Lithium iodide enables regioconvergent C-F bond functionalization of isomeric Morita-Baylis-Hillman fluorides with carbon, sulfur, and nitrogen nucleophiles. The defluorinative carbon-carbon and carbon-heteroatom bond formations give multifunctional compounds in excellent yields and with good to high diastereoselectivities at room temperature. The possibility of catalytic enantioselective allylation is also discussed.

| S-EPMC11301663 | biostudies-literature

Morita-Baylis-Hillman reaction of acrylamide with isatin derivatives.

Project description:The Morita-Baylis-Hillman reaction of acrylamide, as an activated alkene, has seen little development due to its low reactivity. We have developed the reaction using isatin derivatives with acrylamide, DABCO as a promoter and phenol as an additive in acetonitrile. The corresponding aza version with acrylate and acrylonitrile has also been developed resulting in high product yields.

| S-EPMC4273229 | biostudies-literature

Metal catalyst-free N-allylation/alkylation of imidazole and benzimidazole with Morita-Baylis-Hillman (MBH) alcohols and acetates.

Project description:A highly α-regioselective N-nucleophilic allylic substitution of cyclic MBH alcohols and acetates with imidazole or benzimidazole, in toluene at reflux with an azeotropic distillation, was successfully carried out with no catalysts or additives, affording the corresponding N-substituted imidazole derivatives in good yields. On the other hand, in refluxing toluene or methanol, the aza-Michael addition of imidazole onto acyclic MBH alcohols was performed using DABCO as an additive, leading to the corresponding 1,4-adducts in 70-84% yields.

| S-EPMC10477972 | biostudies-literature

Regio- and Stereoselective Electrochemical Alkylation of Morita-Baylis-Hillman Adducts.

Project description:Electrosynthesis is effectively employed in a general regio- and stereoselective alkylation of Morita-Baylis-Hillman compounds. The exposition of N-acyloxyphthalimides (redox-active esters) to galvanostatic electroreductive conditions, following the sacrificial-anode strategy, is proved an efficient and practical method to access densely functionalized cinnamate and oxindole derivatives. High yields (up to 80%) and wide functional group tolerance characterized the methodology. A tentative mechanistic sketch is proposed based on dedicated control experiments.

| S-EPMC9237826 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data