910896-38-7

Upstream product

• 536-74-3 phenylacetylene 
• 1252576-12-7 N-(2-(chloromethyl)-4-methoxyphenyl)-4-methylbenzenesulfonamide 
• 98-88-4 benzoyl chloride 
• 1054567-41-7 (E)-4-methoxy-2-styrylaniline 
• 100-42-5 styrene 
• 32338-02-6 2-bromo-4-methoxyaniline 
• 910896-36-5 N-(4-methoxy-2-(phenylethynyl)phenyl)-4-methylbenzenesulfonamide 
• 1314595-90-8 N-(2-iodo-4-methoxylphenyl)-4-methylbenzenesulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

DMSO/SOCl2-mediated C(sp2)-H amination: Switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives

The reaction of 2-alkenylanilines with SOCl2 in DMSO was found to selectively afford 3-unsubstituted indoles and 3-methylthioindoles. This switchable approach was found to be temperature-dependent: at room temperature, the reaction afforded 3-unsubstituted indoles through intramolecular cyclization and elimination; while at higher temperature, the reaction gave 3-methylthioindoles via further electrophilic methylthiolation.

Tandem Phospha-Michael Addition/N-Acylation/ Intramolecular Wittig Reaction of aza-o-Quinone Methides: Approaches to 2,3-Disubstituted Indoles

A tandem phospha-Michael addition/N-acylation/intramolecular Wittig reaction of in situ formed aza-o-QMs is disclosed. This approach features high functional group tolerance and provides a convenient and practical access to biologically significant indole derivatives (37 examples, up to 91% yield) under mild reaction conditions. (Figure presented.).

2-substituted indole compound and preparation method thereof

The invention provides a 2-substituted indole compound. The compound is of a structure shown as a formula I, wherein R1 is selected from hydrogen, alkoxy, hydroxyl and halogen, and the position and the number of R1 cannot be fixed; R2 is selected from hydrogen, alkyl and C6 aryl; R3 is selected from a C6 aryl group, a C4-C8 heteroaryl group, a C1-C7 alkyl group, a C1-C6 cycloalkyl group, a C8 alkenyl group, a C4 ester group, and a trifluoromethyl group, and the C6 aryl group may have optionally one or more substitutions independently selected from the group consisting of hydrogen, C1 alkoxy, and halogen. The preparation method comprises the following steps: adding a compound shown as a formula A, a solvent, triphenylphosphine, an alkali and a compound shown as a formula B into a reaction flask at room temperature; putting the reaction system in the step (1) into an oil bath pan, uniformly stirring and reacting, and detecting a reaction endpoint by TLC; and taking out the reaction system in the step (2), separating and purifying to obtain the target compound shown in the formula I. The preparation method provided by the invention can be used for efficiently and quickly preparing the2-substituted indole compound.

Nickel-Catalyzed Arylative Additions on 2-Alkynyl-N-Arylsulfonylanilides to Construct Functionalized Indoles

The addition of aryl iodides to 2-alkynyl-N-sulfonylanilides to form 2,3-difunctionalized N-arylsulfonylindoles can be catalyzed using a nickel catalyst ligated to a bis(cyclohexanyl)phosphinoferrocene. A variety of nickel complexes can be used as precata

An efficient synthesis of indoles via a CuMgAl-LDH-catalyzed cyclization of 2-alkynylsulfonanilides

A highly efficient method for the synthesis of indoles has been successfully developed via a CuMgAl-LDH-catalyzed intramolecular annulation reaction of 2-alkynylsulfonanilides. This CuMgAl-LDH catalyst features facile preparation, recovery, and reuse at l

Tandem Sonogashira-Hagihara coupling/cycloisomerization reactions of ethynylboronic acid MIDA ester to afford 2-heterocyclic boronic acid MIDA esters: A concise route to benzofurans, indoles, furopyridines and pyrrolopyridines

A one-pot process that provides direct access to 2-heterocyclic MIDA (N-methyliminodiacetic acid) boronates has been developed. The reaction of 2-iodophenols or 2-iodoanilines with ethynylboronic acid MIDA ester readily afforded 2-substituted heterocyclic compounds. Amidine and phosphazene bases, especially TMG (1,1,3,3-tetramethylguanidine) assumed an important role in the tandem Sonogashira-Hagihara coupling/cycloisomerization reactions.

Metal-free C-H amination for indole synthesis

An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.

METHODS FOR THE SYNTHESIS OF HETEROAROMATIC COMPOUNDS

Methods of making heteroaromatic compounds comprising a 5- membered ring, and dihydro forms thereof, by a metal catalysed 5-endo-cyclisation of alkynes (acetylenes) are disclosed. The methods involve the use of a catalyst comprising a silver salt, more preferably a silver (I) salt, which is employed as a heterogeneous catalyst for the cyclisation reaction. The methods can produce different types of heteroaromatic compounds and are capable of producing highly substituted products, i.e. products in which the 5-membered ring is disubstituted, trisubstituted or, with further simple reactions, tetrasubstituted. The methods described herein generally the advantages that they use conditions and reagents that are benign, cheap and flexible and amenable to scale up, and in which the only by-product is water.