Browse
Submit Data
Databases
API
Help

Dataset Information

35 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines.

ABSTRACT: The metal-free synthesis of 2-substituted and 2,3-disubstituted morpholines through a one-pot strategy is described. A simple and inexpensive ammonium persulfate salt enables the reaction of aziridines with halogenated alcohols to proceed via an SN2-type ring opening followed by cyclization of the resulting haloalkoxy amine.

SUBMITTER: Sun H

PROVIDER: S-EPMC4419545 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines.

Sun Hongnan H Huang Binbin B Lin Run R Yang Chao C Xia Wujiong W

Beilstein journal of organic chemistry 20150422

The metal-free synthesis of 2-substituted and 2,3-disubstituted morpholines through a one-pot strategy is described. A simple and inexpensive ammonium persulfate salt enables the reaction of aziridines with halogenated alcohols to proceed via an SN2-type ring opening followed by cyclization of the resulting haloalkoxy amine. ...[more]

PMID: 25977727

Similar Datasets

Efficient Microwave-assisted One-pot Three-component Synthesis of 2,3-Disubstituted Benzofurans under Sonogashira Conditions.

Project description:An efficient one-pot method for the synthesis of 2,3-disubstituted benzo[b]furans from commercially available 2-iodophenols, terminal acetylenes and aryl iodides has been developed utilizing Sonogashira reaction conditions. After an initial Sonogashira coupling of the 2-iodophenol with the terminal alkyne, cyclization involving the aryl iodide provides the 2,3-disubstituted benzo[b]furan in good to excellent yields. The use of microwave irradiation shortens the reaction times and minimizes the side products. This methodology is especially useful for the construction of libraries of highly substituted benzo[b]furans and their analogues.

| S-EPMC3594699 | biostudies-literature

A one-pot successive cyclization-alkylation strategy for the synthesis of 2,3-disubstituted benzo[<i>b</i>]thiophenes.

Project description:In this study, a new environmentally benign iodine-mediated one-pot iodocyclization/alkylation strategy for the synthesis of benzo[b]thiophene derivatives starting from 2-alkynylthioanisoles was developed. The synthesis of a diverse population of 2,3-disubstituted benzo[b]thiophenes was achieved in high yields by employing moderate reaction conditions using 1,3-dicarbonyl substrates as the nucleophile and various substituted propargyl alcohols as both the cyclization precursor and the alkylating agent. This method resulted in the formation of a series of complex structures obtained in a single step. Additionally, a strategy was devised for the one pot iodocyclization/oxidation of propargyl alcohols into carbonyl functionalized benzo[b]thiophene structures. These green one-pot reaction processes were designed to reduce wastes and byproducts while generating a complex substitution pattern on the benzo[b]thiophene structure. The reported methodologies may be used to synthesize more functionalized benzo[b]thiophene structures that can be used in both biomedical and organic electronic applications.

| S-EPMC8211089 | biostudies-literature

One-Pot Synthesis of Isoxazole-Fused Tricyclic Quinazoline Alkaloid Derivatives via Intramolecular Cycloaddition of Propargyl-Substituted Methyl Azaarenes under Metal-Free Conditions.

Project description:A practical method was developed for the convenient synthesis of isoxazole-fused tricyclic quinazoline alkaloids. This procedure accesses diverse isoxazole-fused tricyclic quinazoline alkaloids and their derivatives via intramolecular cycloaddition of methyl azaarenes with tert-butyl nitrite (TBN). In this method, TBN acts as the radical initiator and the source of N-O. Moreover, this protocol forms new C-N, C-C, and C-O bonds via sequence nitration and annulation in a one-pot process with broad substrate scope and functionalization of natural products.

| S-EPMC10057414 | biostudies-literature

Catalyst-Free One-Pot Synthesis of Densely Substituted Pyrazole-Pyrazines as Anti-Colorectal Cancer Agents.

Project description:The first catalyst-free post-Ugi cascade methodology was developed for expeditious access to structurally diverse and complex pyrazole-pyrazines in one-pot. This novel cascade reaction features an intramolecular N2-arylation of pyrazoles with allenes at the C-β position of triple bond. Screening in the colorectal cancer cell lines HCT116 and SW620 validated the feasibility of the methodology for generating bioactive compounds. The lead compound 7h which is active against HCT116 and SW620 with IC50 of 1.3 and 1.8 µM, respectively, can be synthesized and purified in a gram process synthetic scale in 7 hours. The mechanical studies indicated that compound 7h can induce cell cycle arrest in the G2/M phase and inhibit proliferation and viability in human colon cancer cells. Overall, compound 7h is represented as a promising starting point for the development of new anti-colorectal cancer drugs.

| S-EPMC7283261 | biostudies-literature

Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles.

Project description:The pyrazole scaffold is one of the most prevalent and important tool in medicinal chemistry. Here, we report a method for preparing 3,5-diarylpyrazoles in good to excellent yield by reacting hydrazones of aryl aldehydes with substituted acetophenones in ethanol in the presence of dimethyl sulfoxide/cat. I2/cat. HCl. The reverse process, reacting hydrazones of substituted acetophenones with aryl aldehydes under the same conditions, also provides 3,5-diarylpyrazoles in good to excellent yields. Reaction of hydrazones of aldehydes with 2'-aryloxy ketones in the presence of cat. HCl in ethanol and the catalyst-free reaction of phenacyl bromides with hydrazones of aldehydes in ethanol also gave good to excellent yields of 3,5-diarylpyrazoles.

| S-EPMC6643981 | biostudies-literature

One-pot synthesis of novel 2,3-dihydro-1H-indazoles.

Project description:A copper(I)-mediated one-pot synthesis of 2,3-dihydro-1H-indazole heterocycles has been developed. This synthetic route provides the desired indazoles in moderate to good yields (55%-72%) which are substantially better than those achievable with an alternative two-step reaction sequence. The reaction is tolerant of functionality on the aromatic ring.

| S-EPMC6264256 | biostudies-literature

New strategy for the synthesis of substituted morpholines.

Project description:A four-step synthesis of cis-3,5-disubstituted morpholines from enantiomerically pure amino alcohols is described. The key step in the synthesis is a Pd-catalyzed carboamination reaction between a substituted ethanolamine derivative and an aryl or alkenyl bromide. The morpholine products are generated as single stereoisomers in moderate to good yield. This strategy also provides access to fused bicyclic morpholines as well as 2,3- and 2,5-disubstituted products.

| S-EPMC2709957 | biostudies-literature

Green one pot solvent-free synthesis of pyrano[2,3-c]-pyrazoles and pyrazolo[1,5-a]pyrimidines.

Project description:Pyrano[2,3-c]pyrazoles are obtained via mixing ethyl acetoacetate, hydrazine hydrate, aldehydes or ketones and malononitrile in the absence of solvent. These same products were also obtained by reacting arylidenemalononitriles 3 with 3-methyl-2-pyrazolin-5-ones. NOE difference experiments confirmed that these products exist solely in the 2H form. Similar treatments of 3-amino-2-pyrazolin-5-one with arylidene-malononitrile afforded adduct 6. Similarly mixing ethyl cyanoacetate, hydrazine hydrate, aldehydes, with malononitrile gave the same product 6. A novel synthesis of 4-oxo-4H-pyrano[2,3-c]pyrazole (8) could be achieved via reacting 3-methyl-2-pyrazolin-5-one with a mixture of cyanoacetic acid and acetic anhydride. Similar treatment of 3-aminopyrazole 11 with the benzylidene-malononitrile produced the pyrazolo[2,3-a]pyrimidines 12a,b.

| S-EPMC6257727 | biostudies-literature

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation.

Project description:1,5-Disubstituted indole-2-carboxaldehyde derivatives 1a-h and glycine alkyl esters 2a-c are shown to undergo a novel cascade imination-heterocylization in the presence of the organic base DIPEA to provide 1-indolyl-3,5,8-substituted γ-carbolines 3aa-ea in good yields. The γ-carbolines are fluorescent and exhibit anticancer activities against cervical, lung, breast, skin, and kidney cancer cells.

| S-EPMC8218543 | biostudies-literature

Multicomponent type II anion relay chemistry (ARC): one-pot syntheses of 2,3-disubstituted furans and thiophenes.

Project description:Effective, one-pot syntheses of 2,3-disubstituted furans and thiophenes, exploiting 2-tert-butyldimethylsilyl-3-formylfuran and -thiophene as the respective bifunctional linchpins, have been developed. The synthetic protocol involves multicomponent type II Anion Relay Chemistry (ARC) mediated by a solvent-controlled C(sp(2))-->O 1,4-Brook rearrangement. Simple organolithiums and alpha-disubstituted ester enolates prove effective as the initiating nucleophiles.

| S-EPMC2777545 | biostudies-other

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