1403458-19-4

Upstream product

• 772-38-3 4-tert-Butylphenylacetylene 
• 95-53-4 o-toluidine 
• 615-43-0 2-iodophenylamine 
• 52670-38-9 2-ethynylaniline 
• 3972-65-4 1-bromo-4-tert-butylbenzene 

Downstream Products

• 1610555-79-7 4-butoxy-3-(4-tert-butylphenyl)-2(1H)-quinolinone 
• 1123215-42-8 5,10-bis(4-tert-butylphenyl)-indeno[2,1-a]indene 
• 521295-49-8 2-(4-(tert-butyl)phenyl)-1H-indole 

Relevant academic research and scientific papers

Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones

Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.

Copper(I)-Mediated Cascade Annulation via Dual C-H/C-H Activation: Access to Benzo[a]carbazolic AEEgens

A Cu(I)-mediated cascade cyclization/annulation of unprotectedo-alkynylanilines with maleimides in one pot is developed. The protocol offers sequential formation of one C-N and two C-C bonds to deliver fused benzo[a]carbazoles having free NH skeletons. The annulated products display fluorescence emission in the range of 485-502 nm with a large Stokes shift and fluorescence lifetime of ～17 ns. The annulated3aadisplays AEE behavior in the ethanol/hexane system and possesses marigold-flower-like morphology at the aggregated state. Cell viability assays enumerate biocompatible AEEgens, while their high intracellular fluorescence depicts cell imaging applicability.

Gold(I)-Catalyzed Reactions between N-(o-Alkynylphenyl)imines and Vinyldiazo Ketones to Form 3-(Furan-2-ylmethyl)-1 H-indoles via Postulated Azallyl Gold and Allylic Cation Intermediates

This work describes gold-catalyzed additions of vinyldiazo ketones to N-(o-alkynylphenyl)imines to yield 3-(furan-2-ylmethyl)-1H-indoles involving skeletal rearrangement; these new catalytic reactions are applicable to a wide range of substrates. We postu

An expedient route to tricyanovinylindoles and indolylmaleimides fromo-alkynylanilines utilising DMSO as a one-carbon synthon

A Pd(ii)/Cu(ii) catalysed domino synthesis of tricyanovinylindoles has been achieved using DMSO as a one-carbon synthon. The reaction proceedsviathe construction of 2-aryl-3-formyl indole followed by sequential addition of malononitrile and a CN resulting

Role of substituents present in bidentate ligand frame of Cu(I) catalysts on Sonogashira cross coupling reactions

Cu(I) catalysts {[Cu(L1?4)Cl(PPh3)] where L1?4 = condensed product of 2-(1-phenylhydrazinyl)-pyridine with different benzaldehydes} were synthesized and characterized by 1H NMR, 31P NMR, UV–Vis and IR techniques. Complex 2 structure was authenticated by single crystal X-ray method. Different electron donating and withdrawing substituents are present in the ligand frame of Cu(I) catalysts and their role on Sonogashira reaction was investigated. The efficiency order of catalysts for the coupling reaction was found to be 2 > 1>3 > 4, clearly indicated the role of substituents present in the ligand frame was useful to effectively catalyze the Sonogashira reaction. The products were characterized using 1H NMR and 13C NMR.

Palladium-Catalyzed Ligand-Free Double Cyclization Reactions for the Synthesis of 3-(1′-Indolyl)-phthalides

Indole and phthalide are privileged heterocyclic scaffolds in numerous natural products and bioactive molecules. The synthesis and biological evaluation of the compounds combining these two scaffolds have rarely been reported. Herein, we repot the first palladium-catalyzed ligand-free double cyclization reactions that enable efficient synthesis of 3-(1′-indolyl)-phthalides (42 examples, up to 96% yield) under mild conditions. Notably, only 1.0 mol % of catalyst loading is used, suggesting high efficiency. Late-stage elaborations give highly functionalized analogues.

One-Pot Synthesis of N-Imidoyl-(1 H)-indoles via Palladium-Catalyzed Oxidative Insertion Domino Reaction with Isocyanide and Arylboronic Acid

Efficient one-pot synthesis of N-imidoyl-(1H)-indoles has been described, which is achieved by the palladium-catalyzed oxidative insertion of 2-(phenylethynyl)aniline, arylboronic acid, and isonitrile. This method provides a new way to synthesize N-imidoy

On water: iodine-mediated direct construction of 1,3-benzothiazines from ortho-alkynylanilines by regioselective 6-exo-dig cyclization

Herein, we report the 6-exo-dig ring closure of ortho-alkynylanilines with readily available aroyl isothiocyanate. An environmentally benign, metal- and base-free, iodine promoted cascade synthesis of highly functionalized (benzo[1,3]thiazin-2-yl)benzimid

Cobalt-Catalyzed Enantioselective Hydroboration/Cyclization of 1,7-Enynes: Asymmetric Synthesis of Chiral Quinolinones Containing Quaternary Stereogenic Centers

An asymmetric cobalt-catalyzed hydroboration/cyclization of 1,7-enynes to synthesize chiral six-membered N-heterocyclic compounds was developed. A variety of aniline-tethered 1,7-enynes react with pinacolborane to afford the corresponding chiral boryl-fun

Facile Synthesis of π-Conjugated Quinazoline-Substituted Ethenes from 2-Ethynylanilines and Benzonitriles under Transition-Metal-Free Conditions

A new transition-metal-free version for the synthesis of π-conjugated quinazoline-substituted ethene derivatives from readily available starting materials has been developed. Quinazoline-substituted ethenes were obtained in moderate to high yields with completely Z-selectivity, and the resulting quinazoline-substituted ethenes show typical aggregation-induced emission (AIE) properties.