116491-53-3

Upstream product

• 614-76-6 N-acetyl-2-bromoaniline 
• 35864-20-1 1-hexynyltributyltin 
• 19591-17-4 o-iodoacetanilide 
• 693-02-7 hex-1-yne 
• 116491-50-0 2-(hex-1-ynyl)aniline 
• 75-36-5 acetyl chloride 
• 1241049-26-2 C₁₄H₁₇NO 
• 615-43-0 2-iodophenylamine 

Relevant academic research and scientific papers

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.

Hydroformylation of 2-Alkynylanilines: Toward an Alternative Methodology for the Synthesis of 3-Substituted Indoles

A potentially viable route for the synthesis of 3-substituted indoles is presented herein. The methodology is based on a regioselective Rh-catalysed hydroformylation of prepared 2-alkyn-1-ylanilines. The requisite 2-alkynylaniline substrates were prepared in high yields (>85 %) using the Pd-catalysed Sonogashira reaction. A catalyst complex that comprises RhI(CO)(PPh3)3 and 1,2-bis(diphenylphosphino)ethane as the ligand allowed the quantitative conversions of the alkynyl substrates with selectivities >75 % for the desired 3-substituted indoles.

Practical synthesis of indoles and benzofurans in water using a heterogeneous bimetallic catalyst

This paper describes the preparation of indoles, azaindoles and benzofurans in pure water by using a new heterogeneous Pd-Cu/C catalyst through a cascade Sonogashira alkynylation-cyclization sequence. Details of the optimization studies and the substrate scope are discussed. This procedure allows the preparation of heterocycles with good yields and is tolerant to a wide variety of functional groups.

Multicatalytic one-pot reaction of 1-(2-alkynylphenyl)ketoximes for generation of indole derivatives

Multicatalytic one-pot Beckmann rearrangement/intramolecular cyclization/halogenation reaction of 1-(2-alkynylphenyl)ketoxime is reported, leading to the expected indole derivatives in good yield.

Cupric halide-mediated intramolecular halocyclization of N-electron-withdrawing group-substituted 2-alkynylanilines for the synthesis of 3-haloindoles

A convenient and efficient method for the synthesis of 3-haloindoles has been developed. Both 3-chloro-and 3-bromoindole derivatives can be obtained in high yields by the reaction of N-electron-withdrawing group-substituted 2-alkynylanilines with cupric h

Simple indole synthesis by one-pot sonogashira coupling-NaOH-mediated cyclization

Coupling of o-iodoanilines with terminal alkynes under standard Sonogashira conditions, and further treatment with NaOH under conventional heating or microwave irradiation, afford 2-substituted indoles in usually high yields. Functionalities such as halides, nitro, and cyano groups are tolerated under the reaction conditions. Georg Thieme Verlag Stuttgart.

Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential Sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF).

The sequential Sonogashira reaction and the cyclization reaction of various 2-iodoanilines and terminal alkynes in the presence of a palladium catalyst and tetrabutylammonium fluoride (TBAF) gave the corresponding 2-substituted indoles in good yields.