1621167-90-5

Upstream product

• 2058-74-4 1-methyl-1H-indole-2,3-dione 
• 119375-97-2 4-methylphenylacetylenemagnesium bromide 
• 766-97-2 4-n-methylphenylacetylene 

Relevant academic research and scientific papers

Transition-Metal-Free Cyclization of Propargylic Alcohols with Aryne: Synthesis of 3-Benzofuranyl-2-oxindole and 3-Spirooxindole Benzofuran Derivatives

An unprecedented base-mediated cyclization of propargylic alcohols with aryne is reported, providing a novel method for the synthesis of 3-benzofuranyl-2-oxindole and 3-spirooxindole benzofuran scaffolds via a propargyl Claisen rearrangement/cycloaddition pathway. The nature of the substituent on acetylene group of propargylic alcohol influences the outcome of the reaction. The protocol offers a transition-metal-free and operationally simple methodology with broad substrate scope as a ready access to complex oxindole-linked heterocyclic compounds.

Synthesis of Spirooxindoles Bearing 1,3-Oxathiolane-2-thione Moiety From Isatin-Derived Propargylic Alcohols

Spirooxindoles bearing 1,3-oxathiolane-2-thione moiety were synthesized from isatin-derived propargylic alcohols and carbon disulfide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The spirooxindoles were formed stereoselectively via attack of the alkoxide of propargylic alcohol to carbon disulfide to form xanthate anion and a following 5-exo-dig cyclization process.

Synthesis of isatin-conjugated 3H-indole-N-oxides and their serendipitous conversion to spiroindolenines

Isatin-conjugated 3H-indole-N-oxides were synthesized from isatin-derived propargylic alcohols and nitrosobenzenes in moderate yields. Isatin-conjugated 3H-indole-N-oxides were converted to novel spiroindolenines under PPh3-mediated deoxygenati

An efficient synthesis of dihydrofuranyl spirooxindoles from isatin-derived propargylic alcohols and 1,3-dicarbonyls

Various dihydrofuranyl spirooxindoles have been synthesized via montmorillonite K-10-catalyzed propargylation of 1,3-dicarbonyl compounds with isatin-derived propargylic alcohols and subsequent base-mediated 5-exo-dig cyclization.

Cycloisomerization of Oxindole-Derived 1,5-Enynes: A Calcium(II)-Catalyzed One-Pot, Solvent-free Synthesis of Phenanthridinones, 3-(Cyclopentenylidene)indolin-2-ones and 3-Spirocyclic Indolin-2-ones

Calcium-catalyzed regioselective synthesis of oxindole-derived 1,5-enynes, followed by cycloisomerization, from readily accessible 3-hydroxy-3-(alkynyl)indolin-2-ones and styrenes in one-pot, under solvent-free conditions is described. This method offers the synthesis of diverse molecules: phenanthridinones, 3-(cyclopentenylidene)indolin-2-ones, and 3-spirocyclic indolin-2-ones are obtained through cascade reactions including cross-dehydrative-coupling, [3,3]-sigmatropic rearrangement, carbocyclization, isomerization, oxidative-ring rearrangement, and Diels-Alder cycloaddition. In addition, this method features atom- and step-economy, broad substrate scope, and high yields. (Figure presented.).

Stereoselective and Regioselective Assembly of Spirooxindole [2,1-b]furan Motifs through a Tandem Friedel–Crafts Alkylation/5-exo-dig-Cyclization

3-Alkynyl-3-OBoc (Boc = tert-butoxycarbonyl) oxindole derivatives underwent a CuII-mediated stereo- and regioselective Friedel–Crafts alkylation/5-exo-dig-cyclization with 2-naphthols or cyclic 1,3-diketones. This gave spirooxindole [2,1-b]furan motifs in good to excellent yields under ambient conditions, and the process has a wide substrate scope.

One-pot synthesis of 3-naphtho[2,1-b]furanyl-2-oxindoles from 3-(arylethynyl)-3-hydroxyindolin-2-ones and 2-naphthols

3-Naphthofuranyl-2-oxindoles were synthesized by the reaction of 3-(arylethynyl)-3-hydroxyindolin-2-ones and 2-naphthols via Friedel–Crafts reaction and a following Michael type 5-exo-dig cyclization. In addition, dihydrofuranyl-spirooxindoles were synthesized from 3-(ortho-hydroxyaryl)-2-oxindoles by base-catalyzed cyclization reaction.

Catalytic C-H activation of arylacetylenes: A fast assembly of 3-(arylethynyl)-3-hydroxyindolin-2-ones using CuI/DBU

A highly efficient and atom-economic methodology has been developed for the synthesis of 3-(arylethynyl)-3-hydroxyindolin-2-ones from isatins by C-H activation of arylacetylenes using a catalytic quantity of copper(I) iodide (5 mol%) and DBU (20 mol%) at 25°C, affording the products in excellent yields in very short reaction time (5 min).