Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Base-Mediated Coupling Reactions of Benzenesulfonyl Azides with Proline: Synthesis of Proline-Derived Benzenesulfonamides.

ABSTRACT: Sulfonamides and lipids are widely found in natural products, bioactive substances, and pharmaceuticals. Here, we report N-sulfonylation and esterification of carboxylic acids in an environment-friendly one-pot tandem protocol involving 1,2-dichloroethane (DCE). Moreover, 1,8-diazabicyclo (5.4.0) undec-7-ene was necessary for this reaction as a strong base, which drives the reaction to completion. Although DCE is a very low activity reagent, it acts not only as a solvent but also as a reactant in the reaction. The β-chloroester contained in the reaction product can be easily dissociated to react with N, S, and O atoms, increasing the possibility for subsequent synthesis.

SUBMITTER: Liu H

PROVIDER: S-EPMC8697382 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Base-Mediated Coupling Reactions of Benzenesulfonyl Azides with Proline: Synthesis of Proline-Derived Benzenesulfonamides.

Liu Hongyan H Zhang Bin B Zhao Wei W Yu Xiao X Zhu Wenjing W Xia Chengcai C Zhou Yanmeng Y

ACS omega 20211207 50

Sulfonamides and lipids are widely found in natural products, bioactive substances, and pharmaceuticals. Here, we report <i>N</i>-sulfonylation and esterification of carboxylic acids in an environment-friendly one-pot tandem protocol involving 1,2-dichloroethane (DCE). Moreover, 1,8-diazabicyclo (5.4.0) undec-7-ene was necessary for this reaction as a strong base, which drives the reaction to completion. Although DCE is a very low activity reagent, it acts not only as a solvent but also as a rea ...[more]

PMID: 34963962

Similar Datasets

Divergent synthesis of chiral cyclic azides via asymmetric cycloaddition reactions of vinyl azides.

Project description:Vinyl azides, bearing conjugated azide and alkene functional groups, have been recognized as versatile building blocks in organic synthesis. In general vinyl azides act as 3-atom (CCN) synthons through the fast release of molecular nitrogen and have been extensively utilized in the construction of structurally diverse N-heterocycles. Keeping the azide moiety intact in organic transformations to synthesis chiral azides is an important but challenging task. Herein, we report an enantioselective copper(II)/BOX-catalyzed cycloaddition of vinyl azides, generating diverse chiral cyclic azides. α-Aryl substituted vinyl azides react with unsaturated keto esters through an inverse-electron-demand hetero-Diels-Alder reaction to afford chiral azido dihydropyrans with excellent enatioselectivities. In contrast, cyclohexenyl azides undergo a diastereo- and enantio-selective Diels-Alder reaction giving important azido octahydronaphthalenes with three continuous stereogenic centers. Notable features of these reactions include a very broad scope, mild reaction conditions and 100% atom economy.

| S-EPMC6639305 | biostudies-literature

Synthesis of a biotin-derived alkyne for pd-catalyzed coupling reactions.

Project description:[reaction: see text] An efficient synthesis of a terminal alkyne derived from d-biotin was developed to provide an alternative for carboxyl-based biotinylation. This approach was illustrated by the preparation of alkyne- and alkene-linked phenylalanine derivatives using palladium-catalyzed Sonogashira and Oh methodology. (Strept)avidin binding was observed using soluble and immobilized receptors. These results demonstrate the applicability of carbon-linked biotin derivatives for use in affinity-based purification and bioanalytical applications.

| S-EPMC2523258 | biostudies-literature

Base-catalyzed synthesis of aryl amides from aryl azides and aldehydes.

Project description:Aryl amides have been used as important compounds in pharmaceuticals, materials and in molecular catalysis. The methods reported to prepare aryl amides generally require very specific reagents, and the most popular carboxyl-amine coupling reactions demand stoichiometric activators. Herein, we report that aryl azides react with aldehydes under base-catalyzed conditions to yield aryl amides efficiently. Mechanistic investigations support the formation of triazoline intermediates via azide-enolate cycloaddition, which subsequently undergo rearrangement to give amides by either thermal decomposition (20-140 °C) or aqueous acid work-up at room temperature. The strategy does not require nucleophilic anilines and is especially efficient for highly electron-deficient aryl amides, including perfluoroaryl amides, which are otherwise challenging to synthesize.

| S-EPMC5952891 | biostudies-literature

Access to Carbonyl Azides via Iodine(III)-Mediated Cross-Coupling.

Project description:Herein, we present a prominent metal-free C-N cross-coupling platform that enables access to carbamoyl- and ketoazides from isocyanides or silyl enol ethers and trimethylsilyl azide (TMSN3) with an aid of iodine(III) promoter. This offers a rapid route to a diverse set of synthetically valuable azide decorated fragments with excellent substrate scope and good to excellent yields. The disclosed platform exemplifies the use of TMSN3 for incorporation of the azide fragment without the loss of N2.

| S-EPMC11536401 | biostudies-literature

Synthesis of 1,2,3-triazoles using Grignard reactions through the protection of azides.

Project description:An efficient method to prepare organomagnesium intermediates having a protected azido group is reported. Protection of azido groups with di-(tert-butyl)(4-(dimethylamino)phenylphosphine (amphos) and following iodine-magnesium exchange realized the preparation of organomagnesium intermediates, which served in the synthesis of diverse azides by transformation with various electrophiles followed by deprotection with elemental sulfur. Furthermore, click reactions of azides with alkynes enabled synthesizing a wide variety of 1,2,3-triazoles.

| S-EPMC10424848 | biostudies-literature

Oxidation reactions using polymer-supported 2-benzenesulfonyl-3-(4-nitrophenyl)oxaziridine.

Project description:A thermally stable polymer-supported oxidant has been developed. Polymer-supported 2-benzenesulfonyl-3-(4-nitrophenyl)oxaziridine was applied to microwave-assisted reactions that occurred at high temperatures and was shown to oxidize alkenes, silyl enol ethers, and pyridines to the corresponding epoxides and pyridine N-oxides in excellent to good yields and with much shorter reaction times. It also enabled tetrahydrobenzimidazoles to be oxidatively rearranged to spiro fused 5-imidazolones in a more efficient manner. Recycling of the polymer-supported oxidant is also possible with minimal loss of activity after several reoxidations.

| S-EPMC7185433 | biostudies-literature

Synthesis of distibiranes and azadistibiranes by cycloaddition reactions of distibenes with diazomethanes and azides.

Project description:Cycloaddition reactions of distibene [L(Me2N)GaSb]2 (L = HC[C(Me)NDipp]2; Dipp = 2,6-i-Pr2C6H3)[double bond, length as m-dash] with a series of organoazides RN3 (R = Ph, p-CF3Ph, 1-adamantyl (ada)) yielded azadistibiranes [L(Me2N)GaSb]2NR (R = Ph 1, p-CF3Ph 2, ada 3), whereas Me3SiN3 reacted with insertion into one Ga-Sb bond and formation of L(Me2N)GaSbSb(NSiMe3)Ga(NMe2)L (4). Analogous compounds 5 and 6 formed after heating of 1 and 2 above 60 °C. Prolonged heating of 5 resulted in a [2 + 2] cycloaddition accompanied by elimination of LGa(NMe2)2 and formation of tetrastibacyclobutane 7, while the reaction of 5 with a second equivalent of PhN3 gave heteroleptic azadistibirane 9, which isomerized at elevated temperature to distibene 10. Cycloaddition also occurred in reactions of [L(X)GaSb]2 (X = NMe2, OEt, Cl) with Me3Si(H)CN2, yielding distibiranes [L(X)GaSb]2C(H)SiMe3 (X = NMe211, OEt 12, Cl 13). Compounds 1-13 were characterized by IR, UV-Vis and NMR spectroscopy and sc-XRD. The mechanism of the reaction of [L(Me2N)GaSb]2 with PhN3 and Me3SiN3 and the electronic nature of the resulting compounds were studied by DFT calculations.

| S-EPMC8966720 | biostudies-literature

Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions.

Project description:Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0 -catalyzed cross-coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi-step transformations. Here we introduce base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones. We show that under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.

| S-EPMC8518705 | biostudies-literature

Biaryl Formation via Base-Promoted Direct Coupling Reactions of Arenes with Aryl Halides.

Project description:In the absence of ligand, Cs2CO3-promoted cross-coupling reaction of arenes with cyano-/nitro-substituted aryl halides in DMSO affording biaryls is reported. The cyano/nitro group in biaryls is useful and convenient for further transformation. The formation of dibenzofurans resulting from the reactions between arenes and 1-bromo-2-iodobenzene is also reported. On the basis of control experiments and theoretical studies, a radical mechanism is proposed for the formation of biaryls.

| S-EPMC8223439 | biostudies-literature

Nitrileimines as an alternative to azides in base-mediated click [3 + 2] cycloaddition with methylene active nitriles.

Project description:Nitrileimines were implemented in practical click protocols with oxopropanenitriles for the straightforward 5-amino-1H-pyrazole synthesis via 1,3-dipolar cycloaddition. The reaction proceeds at room temperature in a short time with base catalysis and no chromatographic purification. High purity products were isolated by simple filtration. The selectivity of the reaction was observed.

| S-EPMC9051556 | 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