Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Efficient domino approaches to multifunctionalized fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones.

ABSTRACT: Efficient domino approaches for the synthesis of multifunctionalized tricyclic fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones have been established. The reaction pathways were controlled by varying enaminones with different substituted patterns to give a series of new fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones selectively. The complete anti diastereoselectivity was achieved for the first reaction.

SUBMITTER: Jiang B

PROVIDER: S-EPMC3676681 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Efficient domino approaches to multifunctionalized fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones.

Jiang Bo B Li Qiu-Yun QY Zhang Hao H Tu Shu-Jiang SJ Pindi Suresh S Li Guigen G

Organic letters 20120119 3

Efficient domino approaches for the synthesis of multifunctionalized tricyclic fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones have been established. The reaction pathways were controlled by varying enaminones with different substituted patterns to give a series of new fused pyrroles and dibenzo[b,e][1,4]diazepin-1-ones selectively. The complete anti diastereoselectivity was achieved for the first reaction. ...[more]

PMID: 22260312

Similar Datasets

Regiospecific Synthesis and Structural Studies of 3,5-Dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-ones and Comparison with 1,3-Dihydro-2H-benzo[b][1,4]diazepin-2-ones.

Project description:Nine 3,5-dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-ones (17-25), some of which contain fluoro-substituents, have been regiospecifically prepared by reaction of 2,3-diaminopyridines with ethyl aroylacetates. In two cases, open intermediates have been isolated and these are related to the reaction pathway. The X-ray crystal structure of 1-methyl-4-phenyl-3,5-dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-one (23) has been solved (formula, C15H13N3O; crystal system, monoclinic; space group, C2/c). This is an asymmetric unit constituted by a single nonplanar molecule and its conformational enantiomer due to the presence of the seven-membered diazepin-2-one moiety, which introduces a certain degree of torsion in the adjacent pyridine ring. The 1H, 13C, 15N, and 19F NMR spectra were obtained and the chemical shifts, together with those of the previously published 1,3-dihydro-2H-benzo[b][1,4]diazepin-2-ones (1-16), i.e., a total of 544 values, were successfully compared with the chemical shifts calculated at the gauge invariant atomic orbital (GIAO)/Becke, three-parameter, Lee-Yang-Parr (B3LYP)/6-311++G(d,p) level. The seven-membered ring inversion barrier in 5-benzyl-2-phenyl-3,5-dihydro-4H-pyrido[2,3-b][1,4]diazepin-4-one (25) was determined and, in conjunction with the data from the literature, compared with the B3LYP/6-311++G(d,p) computed values. This allowed the determination of several structural effects. The rotation about the exocyclic N1-CR bond was also calculated and its dynamic properties were discussed.

| S-EPMC7542844 | biostudies-literature

11-(4-Meth-oxy-phen-yl)-3,3-dimethyl-2,3,4,5,10,11-hexa-hydro-1H-dibenzo[b,e][1,4]diazepin-1-one monohydrate.

Project description:In the title compound, C(22)H(24)N(2)O(2)·H(2)O, the co-crystallized water mol-ecule inter-acts with the N and O atoms of the mol-ecule through O(w)-H⋯N, O(w)-H⋯O(meth-yl) and N-H⋯O(w) hydrogen-bonding inter-actions. These hydrogen bonds, along with the inter-molecular N-H⋯O=C hydrogen-bonding inter-actions, connect the mol-ecules into a three-dimensional network. The dihedral angle between the two aromatic rings is 65.46 (10)°.

| S-EPMC3344616 | biostudies-literature

Domino reaction of arylglyoxals with pyrazol-5-amines: selective access to pyrazolo-fused 1,7-naphthyridines, 1,3-diazocanes, and pyrroles.

Project description:New multicomponent domino reactions of arylglyoxals with pyrazol-5-amines have been established, providing selective access to unprecedented pyrazolo-fused 1,7-naphthyridines, 1,3-diazocanes, and pyrroles (up to 52 examples). The unreported dipyrazolo-fused 1,7-naphthyridines were regioselectively synthesized through a special double [3 + 2 + 1] heteroannulation accompanied by direct C-C formation between two electrophilic sites of arylglyoxals. The unusual [3 + 3 + 1 + 1] cyclization resulted in 20 examples of novel dipyrazolo-fused 1,3-diazocanes, whereas pyrrolo[2,3-c]pyrazoles were obtained in good yields by varying arylglyoxals 1 and pyrazol-5-amines 2 in the ratio 1:2. Mechanisms of formation of these three new types of heterocycles are also proposed.

| S-EPMC4059248 | biostudies-literature

Allylic amination and N-arylation-based domino reactions providing rapid three-component strategies to fused pyrroles with different substituted patterns.

Project description:New three-component domino reaction providing divergent approaches to multifunctionalized fused pyrroles with different substituted patterns have been established (40 examples). The direct C(sp(3))-N bond formation was achieved through intermolecular allylic amination in a one-pot operation, and N-arylation of amines was realized by varying N-amino acid enaminones. The reaction is easy to perform simply by mixing three common reactants in acetic acid under microwave heating. The reaction proceeds at fast rates and can be finished within 30 min, which makes workup convenient to give good chemical yields.

| S-EPMC3442375 | biostudies-literature

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents.

Project description:Pyrroles and its fused forms possess antimicrobial activities, they can easily interact with biomolecules of living systems. A series of substituted pyrroles, and its fused pyrimidines and triazines forms have been synthesised, all newly synthesised compound structures were confirmed by spectroscopic analysis. Generally, the compounds inhibited growth of some important human pathogens, the best effect was given by: 2a, 3c, 4d on Gram-positive bacteria and was higher on yeast (C. albicans), by 5c on Gram-negative bacteria and by 5a then 3c on filamentous fungi (A. fumigatus and F. oxysporum). Such results present good antibacterial and antifungal potential candidates to help overcome the global problem of antibiotic resistance and opportunistic infections outbreak. Compound 3c gave the best anti-phytopathogenic effect at a 50-fold lower concentration than Kocide 2000, introducing a safe commercial candidate for agricultural use. The effect of the compounds on DNA was monitored to detect the mode of action.

| S-EPMC8491725 | biostudies-literature

Strongly Polarized π-Extended 1,4-Dihydropyrrolo[3,2-b]pyrroles Fused with Tetrazolo[1,5-a]quinolines.

Project description:A straightforward route to 1,4-dihydropyrrolo[3,2-b]pyrroles comprised of two electron-withdrawing quinoline or tetrazolo[1,5-a]quinoline scaffolds has been developed. The versatile multicomponent reaction affording 1,4-dihydropyrrolo[3,2-b]pyrroles combined with intramolecular direct arylation enables assembly of these products in just three steps from anilines with overall yields exceeding 30%. The planarized, ladder-type heteroacenes possess up to 14 conjugated rings. These nominally quadrupolar materials exhibit efficient fluorescence with wavelengths spanning most of the visible spectrum from green-yellow for the dyes possessing biaryl bridges and orange-red for the fully fused systems. In many cases, the fluorescence quantum yields are large, the solvatofluorochromic effects are strong, and the fluorescence is maintained even in crystalline state. Analysis of the electronic structure of these molecular architectures using quantum chemical methods suggests that the character and position of the flanking heterocycle determine the shape of HOMO and LUMO and their extension to N-aryl substituents, influencing the values of molar absorption coefficient. An experimental study of the two-photon absorption (2PA) properties has revealed that it occurs in the 700-800 nm range with apparent deviation from the Laporte parity selection rule, which may be attributed to Hertzberg-Teller contribution to vibronically allowed 2PA transition.

| S-EPMC11002929 | biostudies-literature

5,7-Dimethyl-2,3-dihydro-1H-1,4-diazepin-4-ium picrate.

Project description:In the cation of the title compound, C(7)H(13)N(2) (+)·C(6)H(2)N(3)O(7) (-), the seven-membered 1,4-diazepine ring forms a twist chair conformation. The two o-nitro groups in the anion are twisted by 35.0?(7) and 36.0?(9)° from the benzene ring. In the crystal, N-H?O hydrogen bonds between the cation and anion along with weak C-H?O hydrogen bonds produce chains along the b axis. C-H?O hydrogen bonds connecting the chains are also present.

| S-EPMC2979234 | biostudies-literature

A new and efficient procedure for the synthesis of hexahydropyrimidine-fused 1,4-naphthoquinones.

Project description:A new and efficient method for the synthesis of hexahydropyrimidine-fused 1,4-naphthoquinones in one step with high yields from the reaction of lawsone with 1,3,5-triazinanes was developed.

| S-EPMC4578459 | biostudies-literature

Four-component domino reaction providing an easy access to multifunctionalized tricyclo[6.2.2.0(1,6)]dodecane derivatives.

Project description:A novel four-component domino reaction has been discovered. The reaction is easy to perform simply by mixing four common reactants and Cs(2)CO(3) in ethylene glycol under microwave heating. The reaction proceeds at fast rates and can be finished within 15-24 min, which makes workup convenient. Four stereogenic centers with one quaternary carbon-amino function have been controlled completely. The stereochemistry has been unequivocally determined by X-ray structural analysis. The resulting tricyclo[6.2.2.0(1,6)]dodecane derivatives are of importance for organic and medicinal research.

| S-EPMC2862086 | biostudies-literature

(11-Methyl-pyrido[2,3-b][1,4]benzo-diazepin-6-yl)(phen-yl)methanone.

Project description:In the title compound, C(20)H(15)N(3)O, the diazepine ring adopts a boat conformation. The dihedral angle between pyridine and benzene rings is 55.2 (1)°. The benzoyl phenyl ring forms dihedral angles of 49.4 (1) and 75.9 (1)°, respectively, with the pyridine and benzene rings. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of C-H⋯N hydrogen bonds.

| S-EPMC3008030 | 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