139376-75-3

Upstream product

• 24423-88-9 1-pyrroline N-oxide 
• 100-39-0 benzyl bromide 
• 109-92-2 ethyl vinyl ether 
• 116614-85-8 ethyl (E)-2-(1-benzylpyrrolidin-2-ylidene)acetate 
• 71032-10-5 (E)-ethyl 6-bromohex-2-enoate 
• 64277-92-5 ethyl (E)-6-iodo-2-hexenoate 
• 100-46-9 benzylamine 

Relevant academic research and scientific papers

Ti(IV) promoted 1,3-dipolar cycloaddition of nitrones to vinyl ethers

The 1,3-dipolar cycloaddition of nitrones to vinyl ethers is accelerated by Ti(IV) species. The efficiency of the catalyst parallels its complexation capacity. The use of Ti((i)prO)2Cl2 favours the formation of trans cycloadducts, presumably through an endo bidentate complex, in which the metal atom is simultaneously coordinated to the vinyl ether and to the cyclic nitrone or the Z isomer of the acyclic nitrones.

Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids

The conditions of the Eschenmoser coupling reaction were studied. The formation of the α-thioiminium ion was achieved faster in the presence of an additive (NaI) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives.

Tandem SN2-Michael Reactions for the Preparation of Simple Five- and Six-Membered-Ring Nitrogen and Sulfur Heterocycles

A one-pot tandem SN2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters.Nitrogen-containing rings are prepared by reaction of the ω-halo-2-alkenoate ester with a primary amine in the presence of triethylamine.The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt.Yields are routinely in the 60-80percent range.Experiments are described which elucidate the chronology of the reaction sequences.Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.

Bis(aryl)alkene compounds

The invention relates to compounds of formula I: STR1 in which m=2-4, n and p, which may be identical or different, are an integer equal to 1, 2 or 3, with the proviso that the sum of n and p is not less than 3 and not more than 5, q=0 or 1, R is a 1,2,3,4-tetrahydro-3-quinazolinyl radical, optionally substituted, a 1,3,4,6,11,11a-hexahydro-1,3-dioxo-2H-pyrazino[1,2,-b]isoquinol-2-yl radical, a 1,2-dihydro-1-oxo-2-phthalazinyl radical, optionally substituted, a 2,6-dioxo-1-piperazinyl radical of formula W: STR2 (R3 is a 2-pyridyl radical or an optionally substituted phenyl radical), a radical of formula Z: STR3 (R4 is a carbamoyl radical, a cyano radical, a hydroxycarbonyl radical or an alkoxycarbonyl radical having 1 to 6 carbon atms), or a radical of formula Y: STR4 (R5 is a 2-pyrimidinyl radical, a 1-isoquinolyl radical, a 2-quinolyl radical, a 2-pyridyl radical, a benzyl radical, optionally substituted, a 2-thiazolyl radical, optionally substituted, or a 2-benzothiazolyl radical) and either R1 and R2, identical or different, each are a substituted phenyl radical, or R1 is a phenyl radical and R2 a 2-pyridyl radical (it being possible for each of these two radicals to be substituted), or R1 and R2, together with the carbon atom to which they are attached, form a fluorene radical. Medicinal products