95969-91-8

Upstream product

• 4891-38-7 phenylpropynoic acid methyl ester 
• 107-11-9 1-amino-2-propene 
• 7342-02-1 3-phenylpropynoic acid phenylamide 
• 201230-82-2 carbon monoxide 
• 932-88-7 1-iodo-2-phenylethyne 
• 536-74-3 phenylacetylene 
• 637-44-5 phenylpropyolic acid 
• 84452-21-1 2-hydroxy-4-phenyl-3-butynenitrile 

Downstream Products

• 142671-85-0 6-Phenyl-2,3,3a,4-tetrahydro-cyclopenta[c]pyrrole-1,5-dione 
• 1263037-03-1 (Z)-3-allyl-5-benzylideneoxazolidine-2,4-dione 
• 77302-27-3 (2E)-N-allyl-3-phenyl acrylamide 
• 190449-96-8 CH₂CHCH₂NHCOC₂C₆H₅Co₂(CO)6 

Relevant academic research and scientific papers

N-triflyl-propiolamides: Preparation and transamidation reactions

N-Trifluoromethylsulfonyl-propiolamides have been prepared by two methods: a) N-triflation of secondary acetylenic carboxanilides, prepared in two steps from terminal alkynes, with triflic anhydride (Tf2O) and b) from terminal alkynes and an aryl or alkyl isocyanate followed by Tf2O in a consecutive one-pot reaction. The title compounds are bench-stable and insensitive to water and alcohols but amenable to transamidation reactions with a wide range of amine nucleophiles. Conversely, they are excellent reagents for the propynoylation of ammonia, primary and secondary amines, anilines, and hydrazines.

Efficient synthesis of alkynyl amides via aminocarbonylation of iodoalkynes

Iodoethynylbenzene as iodoalkyne model compound was aminocarbonylated with tert-butylamine under carbon monoxide atmosphere in the presence of in situ palladium(0) catalysts. The formation of the unsaturated carboxamide (alkynyl amide) is always accompanied by that of the Glaser coupling product, diphenylbutadiyne. The yield of the amide-forming reaction was optimised by the systematic variation of the phosphine ligand, carbon monoxide pressure and temperature. The scope of the reaction was investigated by using various primary and secondary amines including amino acid methyl esters as N-nucleophiles. 17α-(Iodoethynyl)-testosterone was also functionalised by using this methodology providing the corresponding 17α-(carboxamidoethynyl)-testosterone derivatives in up to 96% yields. The reaction was extended to 1-(iodoethynyl)cyclohex-1-ene and 1-iodohex-1-yne. Ethyl iodopropiolate gave the enamine type product by the addition of amine to the alkyne functionality which was formed from the iodoalkyne via deiodination under standard aminocarbonylation conditions. The bromo analogue, bromoethynylbenzene has shown lower reactivity than the corresponding iodo derivative.

Silver-Promoted Synthesis of 5-[(Pentafluorosulfanyl)methyl]-2-oxazolines

The synthesis of 5-[(pentafluorosulfanyl)methyl]-2-oxazolines is reported. The use of a silver promoter allows the intramolecular cyclization of N-[2-chloro-3-(pentafluorosulfanyl)propyl]amide to occur without elimination of the chlorine atom, a reaction

A gold(i)-catalyzed intramolecular oxidation-cyclopropanation sequence of 1,6-enynes: A convenient access to [n.1.0]bicycloalkanes

A gold(i)-catalyzed tandem oxidation/cyclopropanation reaction of 1,6-enynes with an external oxidant has been developed. This quite simple and rapid strategy will provide a safe, mild and versatile avenue to numerous carbo- and hetero [n.1.0]bicyclic frameworks.

Structural factors affecting the selectivities in the palladium(II) catalyzed cyclization of N-alkenyl-2-alkynamides

Palladium catalyzed cyclization of N-alkenyl 2-alkynamides occurred smoothly in the presence of CuCl2 and LiCl affording α-chloroalkylidene-γ-butyrolactams and α-chloroalkylidene-δ-valerolactams stereoselectively. The regioselectivity of the in

2-HYDROXY-4-PHENYL-3-BUTYNENITRILE IN SELECTIVE OXIDATION

The oxidation of 2-hydroxy-4-phenyl-3-butynenitrile with active manganese(IV) oxide is accompanied by the intermediate formation of the unstable 2-oxo-4-phenyl-3-butynenitrile, in which the cyano group is substituted by the residue of the nucleophile present in the reaction.The reaction of 2-hydroxy-4-phenyl-3-butynenitrile with secondary amines in absolute ether is accompanied by isomerization to 2-oxo-4-phenyl-3-butenenitrile with subsequent substitution of the cyano group by the amino group.