Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of 5-aryl-3,3′-bis-indolyl and bis-7-aza-indolyl methanone derivatives from 5-bromo-7-azaindoles via sequential methylenation using microwave irradiation, CAN oxidation, and Suzuki coupling reactions† † Electronic supplementary information (ESI) available. Copies of 1H NMR, 13C NMR, DEPT-135, HRMS spectra for all the new compounds, and single-crystal XRD data for compounds 3b and 4a are provided. CCDC 2191474 and 2102023. For ESI and crystallographic data in CIF or other electronic format see DOI: https://doi.org/10.1039/d2ra05849a

ABSTRACT: A catalyst-free and green chemical method has been developed for the methylenation of indole and N-methyl-7-aza indoles with aqueous formaldehyde afforded respective N,N′-dimethyl-3,3′-bis-7-azaindolylmethanes under microwave irradiation in excellent yield. Subsequent oxidation of the products thus obtained, using one electron chemical oxidant CAN afforded N,N′-dimethyl-3,3′-bis-7-azaindolylmethanone derivatives in excellent yield. This resulted in methanone derivatives with halogen substitution at the aryl ring which when subjected to Suzuki coupling with aryl boronic acids furnished highly functionalized fluorescent biaryl derivatives. Plausible mechanisms, characterization including XRD, and evaluation of photophysical properties of the Suzuki coupled products are described. A catalyst-free methylenation of 7-aza indoles under MW irradiation and CAN oxidation of methylenated products to the respective ketones are achieved. Plausible mechanisms of the reactions and photophysical properties of the products are described.

SUBMITTER: Pavithra E

PROVIDER: S-EPMC9607884 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

3,3-Bis(4-bromo-phenyl-sulfan-yl)-1-methyl-piperidin-2-one.

Project description:In the title compound, C18H17Br2NOS2, the conformation of the piperidin-2-one ring is based on a half-chair with the methyl-ene C atom diagonally opposite the N atom being 0.649?(3)?Å above the plane of the remaining five atoms (r.m.s. deviation = 0.1205?Å). The S atoms occupy axial and bis-ectional positions, and the dihedral angle between the benzene rings of 59.95?(11)° indicates a splayed disposition. Helical supra-molecular chains along the b axis sustained by C-H?O inter-actions is the major feature of the crystal packing. The chains are connected into a three-dimensional architecture by C-H?Br and C-H?? inter-actions.

| S-EPMC3629608 | biostudies-literature

2,4-Bis(4-bromo-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:The title compound, C(20)H(19)Br(2)NO, shows a chair-chair conformation for the aza-bicycle with an equatorial disposition of the 4-bromo-phenyl groups [dihedral angle between the aromatic rings = 16.48 (3)°]. In the crystal, a short Br⋯Br contact [3.520 (4) Å] occurs and the structure is further stabilized by N-H⋯O hydrogen bonds and C-H⋯O inter-actions.

| S-EPMC2969662 | biostudies-literature

2,4-Bis(3-bromo-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:The complete mol-ecule of the title compound, C(20)H(19)Br(2)NO, is generated by crystallographic mirror symmetry, with two C, one O and one N atom lying on the mirror plane. The compound exists in a twin-chair conformation with equatorial dispositions of the 3-bromo-phenyl groups [dihedral angle between rings = 27.37 (3)°]. The packing is stabilized by weak N-H⋯O and C-H⋯O inter-actions.

| S-EPMC2959950 | biostudies-literature

2,4-Bis(2-bromo-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:In the mol-ecular structure of the title compound, C(20)H(19)Br(2)NO, the fused six-membered heterocyclic and cyclo-hexane rings adopt a twin-chair conformation with equatorial orientations of all the substituents. Both the ortho-bromo substituents of the benzene rings are oriented towards the carbonyl group; the dihedral angle between the ring planes is 29.13 (3)°. In the crystal structure, the N-H group does not participate in any hydrogen bonds.

| S-EPMC2959882 | biostudies-literature

Crystal structure of 4,4'-bis-(4-bromo-phen-yl)-1,1',3,3'-tetra-thia-fulvalene.

Project description:The mol-ecule of the title compound, C18H10Br2S4, has a C-shape, with C s mol-ecular symmetry. The dihedral angle between the planes of the di-thiol and phenyl rings is 8.35 (9)°. In the crystal, mol-ecules form helical chains along [001], the shortest inter-actions being π⋯S contacts within the helices. The inter-molecular inter-actions were investigated by Hirshfeld surface analysis. Density functional theory (DFT) was used to calculate HOMO-LUMO energy levels of the title compound and its trans isomer.

| S-EPMC6690463 | biostudies-literature

Bis(dialkylphosphino)ferrocene-Ligated Nickel(II) Precatalysts for Suzuki-Miyaura Reactions of Aryl Carbonates.

Project description:Aryl carbonates, a common protecting group in synthetic organic chemistry, are potentially valuable electrophiles in cross-coupling reactions. Here, after performing a thorough evaluation of different precatalysts, we demonstrate that (dcypf)Ni(2-ethylphenyl)(Br) (dcypf = 1,1-bis-(dicyclohexylphosphino)ferrocene) is an efficient precatalyst for Suzuki-Miyaura reactions using a variety of aryl carbonates as substrates. Mechanistic studies indicate that (dcypf)Ni(2-ethylphenyl)(Br), which contains a bidentate phosphine that binds in a trans geometry, is an effective precatalyst for these reactions for two reasons: (i) it rapidly forms the Ni(O) active species and (ii) it minimizes comproportionation reactions between the Ni(O) active species and both the unactivated Ni(II) precatalyst and on-cycle Ni(II) complexes to form catalytically inactive Ni(I) species. In contrast, the state of the art precatalyst (dppf)Ni(o-tolyl)(Cl) (dppf = 1,1-bis(diphenylphosphino)ferrocene), which contains a bidentate phosphine that binds in a cis geometry, forms Ni(I) species during activation and is essentially inactive for aryl carbonate couplings. Although the exact reasons on a molecular level why the dcypf system is more active than the dppf system are unclear, our results indicate that in general Ni catalysts supported by the dcypf ligand will give better performance for catalytic reactions involving substrates which undergo relatively slow oxidative addition, such as aryl carbonates.

| S-EPMC7304551 | biostudies-literature

(2Z,2'Z)-Diethyl 3,3'-[butane-1,4-diylbis(aza-nedi-yl)]bis-(but-2-enoate).

Project description:The whole mol-ecule of the title β-enamino-ester, C(16)H(28)N(2)O(4), is generated by a crystallographic inversion center, situated at the mid-point of the central C-C bond of the 1,4-diamino-butane segment. There are two intra-molecular N-H⋯O hydrogen bonds that generate S(6) ring motifs. This leads to the Z conformation about the C=C bonds [1.3756 (17) Å]. The mol-ecule is S-shaped with the planar central 1,4-diamino-butane segment [maximum deviation for non H-atoms = 0.0058 (13) Å] being inclined to the ethyl butyl-enonate fragment [C-C-O-C-C=C-C; maximum deviation = 0.0710 (12) Å] by 15.56 (10)°. In the crystal, mol-ecules are linked via C-H⋯O inter-actions, leading to the formation of an undulating two-dimensional network lying parallel to the bc plane.

| S-EPMC3470214 | biostudies-literature

Metal-free oxidative coupling of arylmethylamines with indoles: a simple, environmentally benign approach for the synthesis of 3,3'-bis(indolyl)methanes.

Project description:The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant. The present reaction provides a novel route towards the synthesis of 3,3'-bis(indolyl)methanes in excellent yields of up to 95% via C-C and C-N bond formation. This attractive and environmentally friendly one-pot protocol is a simple procedure that features inexpensive acetic acid as the catalyst and molecular oxygen as the sole oxidant, and it supports a wide substrate scope with the good tolerance of functional groups.

| S-EPMC9054727 | biostudies-literature

Bis(piperidin-1-yl)methanone.

Project description:The title compound, C(11)H(20)N(2)O, is a urea derivative bearing two piperidine moieties in place of the amino groups. The mol-ecule shows approximate non-crystallographic C(2) symmetry. The six-membered rings adopt (1)C(4) and (4)C(1) conformations and their mean planes make a dihedral angle of 35.87 (5)°. In the crystal, inter-molecular C-H⋯O contacts connect the mol-ecules into infinite strands along the a axis.

| S-EPMC3051571 | biostudies-literature

2,4-Bis(2-bromo-phen-yl)-7-tert-pentyl-3-aza-bicyclo-[3.3.1]nonan-9-one.

Project description:The title compound, C(25)H(29)Br(2)NO, is a tert-pentyl analog of 2,4-bis-(2-bromo-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one [Par-thiban et al. (2008 ▶). Acta Cryst. E64, o2385]. Similar to its analog, the title compound exists in a twin-chair conformation with an equatorial orientation of the 2-bromo-phenyl groups. The benzene rings are inclined to each other at a dihedral angle of 29.6 (3)°. The tert-pentyl group on the cyclo-hexa-none ring also adopts an exocyclic equatorial disposition.

| S-EPMC3470318 | 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