53330-45-3

Upstream product

• 21375-88-2 1-bromo-2-(phenylethenyl)benzene 
• 55-21-0 benzamide 
• 536-74-3 phenylacetylene 
• 13141-38-3 2-phenylethynylaniline 
• 615-43-0 2-iodophenylamine 
• 35010-17-4 1-nitro-2-phenylethynyl-benzene 
• 4231-62-3 1-benzoyl-1H-benzotriazole 
• 95-14-7 1,2,3-Benzotriazole 
• 93-97-0 benzoic acid anhydride 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 64097-92-3 2-(1-phenylvinyl)aniline 
• 1392323-07-7 N-(2-(1-phenylvinyl)phenyl)benzamide 
• 1885-29-6 anthranilic acid nitrile 
• 33348-34-4 4-amino-3-iodobenzonitrile 

Downstream Products

• 948-65-2 2-phenyl-indole 

Relevant academic research and scientific papers

Preparation method of N-acyl indole compound

The invention discloses a preparation method of an N-acyl indole compound. The preparation method comprises the following steps: adding a palladium catalyst, potassium carbonate, a carbon monoxide substitute, 2-alkynylaniline and an aryl iodide into an or

PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles

An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1–2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates.

Water-Soluble Hypervalent Iodine(III) Having an I-N Bond. A Reagent for the Synthesis of Indoles

A readily accessible and bench-stable water-soluble hypervalent iodine(III) reagent (phenyliodonio)sulfamate (PISA) with an I-N bond was synthesized, and its structure was characterized by X-ray crystallography. With PISA, various indoles were synthesized via C-H amination of 2-alkenylanilines involving an aryl migration/intramolecular cyclization cascade with excellent regioselectivity in aqueous CH3CN. Notably, using this new method as the key step, not only two drug molecules, indometacin and zidometacin, but also another bioactive molecule, pravadoline, were synthesized.

Fluorine as a Traceless Directing Group for the Regiodivergent Synthesis of Indoles and Tryptophans

Despite ample evidence for the unique reactivity offered by hypervalent F-iodanes, mechanistic investigations fall far behind. In order to shed light on the unusual behavior of such F-reagents, we conducted computational and experimental studies on the chemodivergent transformation of styrenes. We identified the spirocyclic F-cyclopropane as the common intermediate for both the C,H-fluorination and C,H-amination pathways. The fate of this key compound is determined by the extent of cationic charge delocalization controlled by the N-substituents. Exploiting this phenomenon, a multitude of different transformations have become available, leading, i.e., to the regiodivergent synthesis of indoles and tryptophans.

Regioselective Synthesis of 2-Substituted Indoles from Benzotriazoles and Alkynes by Photoinitiated Denitrogenation

Herein, we describe a photoinitiated and regioselective synthesis of 2-substituted indoles under mild reaction conditions. This biologically privileged scaffold was accessed in good yields from N-aroylbenzotriazoles, a quencher class previously identified using our mechanism-based luminescence screening, and terminal alkynes in the presence of a photocatalyst and blue light irradiation. This straightforward protocol displays a broad substrate scope and functional group tolerance. Furthermore, the mildness and robustness of the reaction were assessed by the application of an additive-based robustness screen. The determination of the reaction quantum yield and Stern-Volmer studies support the proposed photoinitiated radical chain mechanism.

Intramolecular cooperative C-C bond cleavage reaction of 1,3-dicarbonyl compounds with 2-iodoanilines to give o-(N-Acylamino)aryl ketones and multisubstituted indoles

A copper-catalyzed C-C bond cleavage reaction of 1,3-dicarbonyl compounds with 2-iodoanilines was developed. In this process, the ortho effect played an important role in the reactivity and a new reaction pathway that involved a (2-aminophenyl)-bis-(1,3-dicarbonyl) copper species was clearly observed by a time-course HRMS analysis of the reaction mixture. Unlike the previous reports, both the nucleophilic and electrophilic parts of the 1,3-dicarbonyl compound were coupled with 2-iodoaniline by C-C bond cleavage to form o-(N-acylamino)aryl ketones, which could be efficiently converted into multisubstituted indoles.

Silver(I)-mediated C-H amination of 2-alkenylanilines: Unique solvent-dependent migratory aptitude

A highly effective silver(I)-mediated C-H amination of 2-alkenylanilines has been developed to afford a diverse range of substituted indoles. High functional group tolerance, broad substrate scope, simple/fast/high-yielding reaction, and recovery/reuse of the inexpensive silver oxidant are noteworthy. Furthermore, an uncommon migratory process of β-monosubstituted 2-alkenylanilines with solvent-dependence was demonstrated.

The PdCl2-catalyzed sequential heterocyclization/Michael addition cascade in the synthesis of 2,3-disubstituted indoles

A cascade reaction of 2-N-unprotected-2-alkynylanilines and various electron-deficient alkenes in the presence of PdCl2 provided 2,3-disubstituted indole derivatives, whereas, in the presence of Pd(OAc) 2, the same reaction resulted in the production of N-alkylated-2-alkynylaniline derivatives.

Cesium carbonate-promoted hydroamidation of alkynes: Enamides, indoles and the effect of iron(III) chloride

A series of enamide derivatives was prepared by a simple procedure for the hydroamidation of alkynes with amides and sulfonamides. The use of such a mild base as cesium carbonate promotes the latter transformation, and the addition of catalytic amounts of iron(III) chloride has a beneficial effect in the outcome of some of the presented hydroamidation reactions. A range of indoles was also synthesized from ortho-alkynylanilides by both complementary procedures, which proved to be useful for the construction of the indolo[1,2-c]quinazoline tetracyclic system from an ortho-(2-aminophenylalkynyl)anilide. Copyright

Copper-catalyzed N-arylation/hydroamin(d)ation domino synthesis of indoles and its application to the preparation of a Chekl/KDR kinase inhibitor pharmacophore

Inexpensive copper catalysts allow for efficient syntheses of N-aryl-, N-acyl-, or N-H-(aza)in-doles starting from ortho-alkynylbromoarenes. The broad scope of this domino N-arylation/hydro-amin(d)ation process is highlighted by the synthesis of highly fu