Browse
Submit Data
Databases
API
Help

Dataset Information

25 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

One-pot synthesis of 2-amino-indole-3-carboxamide and analogous.

ABSTRACT: An efficient one-pot, two-step solution-phase synthetic method was developed to synthesize twenty-three 2-amino-indole-3-carboxamides (3) from 2-halonitrobenzene (1) or heterocyclic analogous and cyanoacetamides (2). In this sequence, first, intermediate 2-cyano-2-(2-nitrophenyl)acetamide (4) was generated under basic condition via S(NAr) reaction; after direct addition of hydrochloric acid solution, FeCl(3), and Zn powder, indole 3 was generated via reduction/cyclization process.

SUBMITTER: Wang K

PROVIDER: S-EPMC3124116 | biostudies-literature | 2011 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

One-pot synthesis of 2-amino-indole-3-carboxamide and analogous.

Wang Kan K Herdtweck Eberhardt E Dömling Alexander A

ACS combinatorial science 20101217 2

An efficient one-pot, two-step solution-phase synthetic method was developed to synthesize twenty-three 2-amino-indole-3-carboxamides (3) from 2-halonitrobenzene (1) or heterocyclic analogous and cyanoacetamides (2). In this sequence, first, intermediate 2-cyano-2-(2-nitrophenyl)acetamide (4) was generated under basic condition via S(NAr) reaction; after direct addition of hydrochloric acid solution, FeCl(3), and Zn powder, indole 3 was generated via reduction/cyclization process. ...[more]

PMID: 21395342

Similar Datasets

Three-Component One-Pot Synthesis of Highly Functionalized Bis-Indole Derivatives.

Project description:In this study, we detail the development of a concise and efficient three-component protocol for the regioselective synthesis of highly functionalized bis-indoles through a one-pot, two-step sequential process starting from enaminones 1, indoles 2, and acenaphthylene-1,2-dione 3 that is catalyzed by piperidine and p-methyl benzenesulfonic acid. This protocol has several advantages including simplicity of experimental operation, high efficiency of bond formation, ready availability and low cost of starting materials, environmentally benign conditions, and target molecular diversity.

| S-EPMC6682060 | biostudies-literature

Pot economy and one-pot synthesis.

Project description:The one-pot synthesis of a target molecule in the same reaction vessel is widely considered to be an efficient approach in synthetic organic chemistry. In this review, the characteristics and limitations of various one-pot syntheses of biologically active molecules are explained, primarily involving organocatalytic methods as key tactics. Besides catalysis, the pot-economy concepts presented herein are also applicable to organometallic and organic reaction methods in general.

| S-EPMC5529999 | biostudies-other

Multicomponent versus domino reactions: One-pot free-radical synthesis of ?-amino-ethers and ?-amino-alcohols.

Project description:Following an optimized multicomponent procedure, an aryl amine, a ketone, and a cyclic ether or an alcohol molecule are assembled in a one-pot synthesis by nucleophilic radical addition of ketyl radicals to ketimines generated in situ. The reaction occurs under mild conditions by mediation of the TiCl4/Zn/t-BuOOH system, leading to the formation of quaternary ?-amino-ethers and -alcohols. The new reaction conditions guarantee good selectivity by preventing the formation of secondary products. The secondary products are possibly derived from a competitive domino reaction, which involves further oxidation of the ketyl radicals.

| S-EPMC4311587 | biostudies-literature

Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: Concise synthesis of alangiobussinine.

Project description:The carboline ring system is an important pharmacophore found in a number of biologically important targets. Development of synthetic routes for the preparation of these compounds is important in order to prepare a range of analogues containing the carboline heterocyclic moiety. A manganese dioxide mediated one-pot method starting with an activated alcohol and consisting of alcohol oxidation, Pictet-Spengler cyclisation, and oxidative aromatisation, offers a convenient process that allows access to ?-carbolines. This one-pot process for the preparation of methyl 9H-pyrido[3,4-b]indole-1-carboxylate has subsequently been used as the key step in the synthesis of alangiobussinine and a closely related analogue.

| S-EPMC3201054 | biostudies-other

One-pot synthesis of (-)-Ambrox.

Project description:(-)-Ambrox is recognised as the prototype of all ambergris odorants. Widely used in perfumery, (-)-Ambrox is an important ingredient due to its unique scent and excellent fixative function. An environmentally friendly and practical preparation of (-)-Ambrox is still unavailable at present although a lot of attention has been paid to this hot research topic for many years. A one-pot synthesis of (-)-Ambrox was studied starting from (-)-sclareol through oxidation with hydrogen peroxide in the presence of a quaternary ammonium phosphomolybdate catalyst {[C5H5NC16H33] [H2PMo12O40]}, which gave the product a 20% overall yield.

| S-EPMC5007644 | biostudies-literature

Ultrasound assisted one-pot synthesis of benzo-fused indole-4, 9-dinones from 1,4-naphthoquinone and α-aminoacetals.

Project description:A one-pot synthesis of benzo[f]indole-4,9-diones from 1,4-naphthoquinone with α-aminoacetals has been developed. This method provides a straightforward synthesis of benzo[f]indole-4,9-diones via intramolecular nucleophilic attack of aminoquinones to aldehydes under mild reaction conditions. The detailed mechanism was also investigated.

| S-EPMC8158052 | biostudies-literature

Fluorous-Assisted One-Pot Oligosaccharide Synthesis.

Project description:A new method for oligosaccharide assembly that combines the advantages of one-pot synthesis and fluorous separation is described. After one-pot glycosylations are completed, a fluorous tag is introduced into the reaction mixture to selectively "catch" the desired oligosaccharide, which is rapidly separated from non-fluorous impurities by fluorous solid-phase extraction (F-SPE). Subsequent "release" of the fluo rous tag and F-SPE achieved the purification of the desired oligosaccharide without the use of time- and solvent-consuming silica gel chromatography. Linear and branched oligosaccharides have been synthesized with this approach in just a few hours (for the overall oligosaccharide assembly and purification process).

| S-EPMC3324286 | biostudies-literature

Stereoselective one-pot synthesis of polypropionates.

Project description:Polypropionates-motifs with alternating methyl and hydroxy groups-are important segments of many natural products possessing high bioactivity and therapeutic value. Synthetic access to these structures remains an area of intensive interest, focusing on the establishment of the contiguous stereocentres and a desire for operational simplicity. Here we report an efficient strategy for the stereoselective assembly of polypropionates with three or four stereocentres through a three-step relay process that include Diels-Alder reaction, silylenol ether hydrolysis and Baeyer-Villiger oxidation. The stereochemistry and functionality of the resulting polypropionates depend on the substitution pattern of the diene and dienophile substrates of the Diels-Alder cycloaddition. More importantly, the relay sequence is effectively performed in one pot, and the product could potentially undergo the same sequence for further elaboration. Finally, the C1-C9 segment of the macrolide etnangien is constructed with four of the six stereogenic centres established using the relay sequence.Polypropionates are present in many natural products possessing high bioactivity and therapeutic value. Here the authors show a strategy for the stereoselective assembly of polypropionates with three or four stereocentres through a process that includes a Diels-Alder reaction, silylenol ether hydrolysis and Baeyer-Villiger oxidation.

| S-EPMC5612996 | biostudies-literature

One-pot synthesis of amino acid precursors with insoluble organic matter in planetesimals with aqueous activity.

Project description:The exogenous delivery of organic molecules could have played an important role in the emergence of life on the early Earth. Carbonaceous chondrites are known to contain indigenous amino acids as well as various organic compounds and complex macromolecular materials, such as the so-called insoluble organic matter (IOM), but the origins of the organic matter are still subject to debate. We report that the water-soluble amino acid precursors are synthesized from formaldehyde, glycolaldehyde, and ammonia with the presence of liquid water, simultaneously with macromolecular organic solids similar to the chondritic IOM. Amino acid products from hydrothermal experiments after acid hydrolysis include α-, β-, and γ-amino acids up to five carbons, for which relative abundances are similar to those extracted from carbonaceous chondrites. One-pot aqueous processing from simple ubiquitous molecules can thus produce a wide variety of meteoritic organic matter from amino acid precursors to macromolecular IOM in chondrite parent bodies.

| S-EPMC5357131 | biostudies-literature

The synthesis of HMF-based α-amino phosphonates <i>via</i> one-pot Kabachnik-Fields reaction.

Project description:The first use of biomass-derived HMF in the one-pot Kabachnik-Fields reaction is reported here. A wide range of furan-based α-amino phosphonates were prepared in moderate to excellent yields under mild, effective and environmentally-benign conditions: iodine as a non-metal catalyst, biobased 2-MeTHF as the solvent and room or moderate temperature. The hydroxymethyl group of HMF persists in the Kabachnik-Fields products, widening the scope of further modification and derivatization compared to those arising from furfural. Issues involving the diastereoselectivity and double Kabachnik-Fields condensation were also faced.

| S-EPMC9085609 | 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