Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents.

ABSTRACT: Readily available triethylammonium thiolates were proven to be new and eco-friendly sulfenylating agents for the efficient and practical construction of sulfenylated indoles and pyrroles (48 examples) with good to excellent yields under metal-free and microwave irradiation conditions. The combination of I2 and DMSO enabled direct C-S bond formation, allowing easy and low-cost access to new functionalized C,S-tethered bisindoles and pyrrole-indole pairs with a wide diversity of substituents. The mechanism involving S-S and S-I bond-forming/breaking events was proposed.

SUBMITTER: Fan W

PROVIDER: S-EPMC5624724 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

I2-Catalyzed sulfenylation of indoles and pyrroles using triethylammonium thiolates as sulfenylating agents.

Fan Wei W Yang Zhen Z Jiang Bo B Li Guigen G

Organic chemistry frontiers : an international journal of organic chemistry 20170220 6

Readily available triethylammonium thiolates were proven to be new and eco-friendly sulfenylating agents for the efficient and practical construction of sulfenylated indoles and pyrroles (48 examples) with good to excellent yields under metal-free and microwave irradiation conditions. The combination of I2 and DMSO enabled direct C-S bond formation, allowing easy and low-cost access to new functionalized C,S-tethered bisindoles and pyrrole-indole pairs with a wide diversity of ...[more]

PMID: 28983405

Similar Datasets

Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles.

Project description:A stereospecific palladium-catalyzed N-vinylation of azaheterocycles with vinyl triflates is described. Cyclic and acyclic vinyl triflates along with nonnucleophilic azaheterocycles were found to be substrates for this palladium-catalyzed synthesis of N-vinyl pyrrole and indole derivatives.

| S-EPMC5548004 | biostudies-literature

Rh2(S-biTISP)2-catalyzed asymmetric functionalization of indoles and pyrroles with vinylcarbenoids.

Project description:Asymmetric functionalization of N-heterocycles by vinylcarbenoids in the presence of catalytic amounts of Rh(2)(S-biTISP)(2) has been successfully developed. This bridged dirhodium catalyst not only selectively enforces the reaction to occur at the vinylogous position of the carbenoid but also affords high levels of asymmetric induction.

| S-EPMC3351204 | biostudies-literature

Phosphine-free palladium-catalyzed C-H bond arylation of free (N-H)-indoles and pyrroles.

Project description:This paper describes a phosphine-free palladium-catalyzed method for direct C-arylation of free (N-H)-indoles and pyrroles with iodo- and bromoarene donors. Employing commercially available materials, this new and operationally simple procedure provides a rapid entry to a wide range of C-arylated (N-H)-indoles including derivatives of tryptamine. In the course of this study, a profound halide effect was uncovered, affecting both the efficiency and regioselectivity of indole arylation.

| S-EPMC2971669 | biostudies-literature

Cascade bicyclization of triethylammonium thiolates with hydrazines: efficient access to pyrazolo[3,4-c]quinolines.

Project description:A new bicyclization strategy has been established, allowing a flexible and practical approach to 33 examples of pyrazolo[3,4-c]quinolines from low-cost and readily accessible triethylammonium thiolates with hydrazines. Notably, the features of this work include broad functional group compatibility, mild reaction conditions and good reaction yields.

| S-EPMC5113139 | biostudies-literature

Gold(I)-Catalyzed Synthesis of 3-Sulfenyl Pyrroles and Indoles by a Regioselective Annulation of Alkynyl Thioethers.

Project description:The combination of nucleophilic nitrenoids and π-acid catalysis has emerged as a powerful tool in heterocycle synthesis. Accessing more varied heterocycle-substitution patterns by maintaining the same reaction pathways across different alkynes remains a challenge. Here we show that Au(I) catalysis of isoxazole-based nitrenoids with alkynyl thioethers provides controlled access to (3 + 2) annulation by a regioselective addition β to the sulfenyl group. The reaction with isoxazole-containing nitrenoids delivers sulfenylated pyrroles and indoles as single regioisomers bearing useful functional groups and structural variety.

| S-EPMC8291588 | biostudies-literature

Copper-catalysed regioselective sulfenylation of indoles with sodium sulfinates.

Project description:A copper-catalysed sulfenylation of indoles with sodium sulfinates that affords 3-sulfenylindoles in good-to-excellent yields in N,N-dimethyl formamide (DMF) is described. In the process, DMF serves not only as a solvent but also as a reductant. This transformation is easy to carry out and has mild reaction conditions and good functional group tolerance.

| S-EPMC5990840 | biostudies-literature

Palladium-catalyzed dynamic kinetic asymmetric transformations of vinyl aziridines with nitrogen heterocycles: rapid access to biologically active pyrroles and indoles.

Project description:We report that nitrogen heterocycles can serve as competent nucleophiles in the palladium-catalyzed dynamic kinetic asymmetric alkylation of vinyl aziridines. The resulting alkylated products were obtained with high regio-, chemo-, and enantioselectivity. Both substituted 1H-pyrroles and 1H-indoles were successfully employed to give exclusively the branched N-alkylated products. The synthetic utility of this process was demonstrated by applying this method to the preparation of several medicinal chemistry lead compounds and bromopyrrole alkaloids including longamide B, longamide B methyl ester, hanishin, agesamides A and B, and cyclooroidin.

| S-EPMC2975595 | biostudies-literature

Carbon Atom Insertion into Pyrroles and Indoles Promoted by Chlorodiazirines.

Project description:Herein, we report a reaction that selectively generates 3-arylpyridine and quinoline motifs by inserting aryl carbynyl cation equivalents into pyrrole and indole cores, respectively. By employing α-chlorodiazirines as thermal precursors to the corresponding chlorocarbenes, the traditional haloform-based protocol central to the parent Ciamician-Dennstedt rearrangement can be modified to directly afford 3-(hetero)arylpyridines and quinolines. Chlorodiazirines are conveniently prepared in a single step by oxidation of commercially available amidinium salts. Selectivity as a function of pyrrole substitution pattern was examined, and a predictive model based on steric effects is put forward, with DFT calculations supporting a selectivity-determining cyclopropanation step. Computations surprisingly indicate that the stereochemistry of cyclopropanation is of little consequence to the subsequent electrocyclic ring opening that forges the pyridine core, due to a compensatory homoaromatic stabilization that counterbalances orbital-controlled torquoselectivity effects. The utility of this skeletal transform is further demonstrated through the preparation of quinolinophanes and the skeletal editing of pharmaceutically relevant pyrroles.

| S-EPMC8343525 | 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

Pd(II)-catalyzed C-H iodination using molecular I2 as the sole oxidant.

Project description:Pd-catalyzed ortho-C-H iodination directed by a weakly coordinating amide auxiliary using I2 as the sole oxidant was developed. This reaction is compatible with a wide range of heterocycles including pyridines, imidazoles, oxazoles, thiazoles, isoxazoles, and pyrazoles.

| S-EPMC3762701 | biostudies-literature