3876-61-7

Upstream product

• 3623-15-2 phenyl propargyl ketone 
• 100-52-7 benzaldehyde 
• 89530-34-7 1-phenyl-3-trimethylsilylprop-2-yn-1-ol 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 10508-57-3 3-bromo-1-phenyl-prop-2-yn-1-ol 

Downstream Products

• 41658-08-6 1-Phenyl-3,3-di-β-naphthyloxy-2-propen-1-on 
• 41658-07-5 1-Phenyl-3,3-diphenoxy-2-propen-1-on 
• 95893-84-8 4-Phenyl-2-p-tolyl-[1,3]thiazine-6-thione 
• 94637-25-9 3-mercapto-3-methoxy-1-phenyl-2-propen-1-one 
• 100-47-0 benzonitrile 
• 52039-44-8 2,4-diphenyl-6-thioxo-6H-1,3-thiazin 
• 19036-86-3 2,4-bis(benzoylmethylene)-1,3-dithietane 
• 132361-39-8 2-(4-Chloro-phenyl)-4-phenyl-[1,3]thiazine-6-thione 
• 119729-65-6 1,1-bis(4-amino-5-phenyl-1,2,4-triazol-3-ylthio)-2-benzoylethylene 
• 121033-67-8 2-benzoylmethylene-5-phenyl-3H-1,3,4-thiadiazolo<2,3-d>-1H(2H)-1,2,4-triazolium bromide 
• 35262-47-6 2-benzoylmethylenebenzo-1,3-dithiole 
• 132361-41-2 2-(4-Nitro-phenyl)-4-phenyl-[1,3]thiazine-6-thione 

Relevant academic research and scientific papers

Metal-free synthesis of activated ynesulfonamides and tertiary enesulfonamides

An operationally simple synthesis of activated ynesulfonamides and enesulfonamides is described. Ynesulfonamides can be obtained through reaction of sulfonylamides with activated bromoalkynes and Triton B in a short time at room temperature. Likewise, terminal alkynes react with sulfonylamides to provide enesulfonamides. Z/E enesulfonamides can be transformed exclusively into E enesulfonamides.

Direct spirocyclization from keto-sulfonamides: An approach to azaspiro compounds

Spontaneous spirocyclization of keto-sulfonamides via ynamides through a one-pot process is presented. Push-pull ynamides were obtained through Michael addition/elimination without Cu. The obtained azaspiro compounds are building blocks for indole alkaloids. Theoretical studies provide insights into the mechanism of the formal Conia-ene reaction.

Copper-catalyzed cross-coupling of vinylsiloxanes with bromoalkynes: Synthesis of enynes

Enynes are versatile building blocks in organic synthesis. A copper-catalyzed Hiyama-type cross-coupling of vinylsiloxanes with bromoalkynes is presented. This mild and efficient method led to the formation of various sensitive enynes. The use of cis, trans, and 1,1′-disubstituted vinylsiloxanes was allowed, and full retention of stereochemistry was observed. Sensitive groups such as halides, unsaturated ketones, and aldehydes were fully tolerated.

Organocatalytic asymmetric direct α-alkynylation of cyclic β-ketoesters

The first organocatalytic enantioselective direct α-alkynylation of β-ketoesters and 3-acyl oxindoles is described. It is demonstrated that activated β-halo-alkynes undergo nucleophilic acetylenic substitution catalyzed by chiral phase-transfer compounds to afford the alkynylated products in high yields and excellent enantioselectivities. The potential of the reaction is first demonstrated for various alkynylating reagents having chloride and bromide as the leaving groups and substituents such as allyl and alkyl esters, amides, ketones, and sulfones. These reactions proceed with 74-99% yield and 88-97% ee. Then the scope in nucleophile is demonstrated for a large number of cyclic β-ketoesters with various ring-sizes and for oxindoles as well. The corresponding optically active products are formed in high yields and with enantioselectivities up to 98% ee. The procedure allows for the stereocontrolled attachment of an ethynyl unit in the α-position to the carbonyl compound by facile removal of the activating group, and this has been demonstrated for a number of the optically active allyl esters. Furthermore, the synthesis of optically active 1,4-enynes is also shown. The isolation and characterization by X-ray analysis of the catalyst with p-nitrophenolate as the counterion allowed us to propose a model of the catalyst-substrate intermediate which might account for the observed enantioselectivity of the organocatalytic enantioselective α-alkynylation reaction. Furthermore, it is suggested that this intermediate is also the reactive species for a number of other electrophiles adding to β-ketoesters giving enantioselectivities in the range of 90-98% ee.

Synthesis of substituted 2-amino-1,3-thiazine-6-thiones

The reaction of thiourea with 1-acyl-2-bromoacetylenes in AcOH in the presence of BF3 · Et2O affords 2-amino-4-phenyl(2-thienyl)-1,3-thiazine-6-thiones in high yields.

VALENT ISOMERIZATION OF CARBONYL-CONTAINING NORBORNADIENES

Norbornadiene derivatives containing aldehydic and ketonic groupings at one of the double bonds were synthesized.On irradiation by filtered light from a mercury lamp in the region of the maximum of the long wave absorption band, the compounds obtained iso