83680-97-1

Upstream product

• 3058-39-7 4-iodobenzonitrile 
• 83665-66-1 (E)-4-(3-(1,3-dioxoisoindolin-2-yl)prop-1-enyl)benzonitrile 
• 623-00-7 4-bromobenzenecarbonitrile 

Downstream Products

• 1417560-21-4 (E)-N-(3-(4-cyanophenyl)allyl)acetamide 

Relevant academic research and scientific papers

Catalytic Diastereo- and Enantioselective Fluoroamination of Alkenes

The stereoselective synthesis of syn-β-fluoroaziridine building blocks via chiral aryl iodide-catalyzed fluorination of allylic amines is reported. The method employs HF-pyridine as a nucleophilic fluoride source together with mCPBA as a stoichiometric oxidant, and affords access to arylethylamine derivatives featuring fluorine-containing stereocenters in high diastereo- and enantioselectivity. Catalyst-controlled diastereoselectivity in the fluorination of chiral allylic amines enabled the preparation of highly enantioenriched 1,3-difluoro-2-amines bearing three contiguous stereocenters. The enantioselective catalytic method was applied successfully to other classes of multifunctional alkene substrates to afford anti-β-fluoropyrrolidines, as well as a variety of 1,2-oxyfluorinated products.

The Heck reaction of polymer-supported allylamine with aryl iodides

The Heck reaction of Wang resin-bound allylamine with aryl iodides produces various, substituted cinnamylamines. The catalyst and additive system consisting of palladium(II) acetate, n-Bu4NOAc and potassium chloride, in addition to potassium carbonate in N,N-dimethylformamide, accomplishes a regioselective γ-arylation. By utilising the easily formed and stable carbamate linker on Wang resin, the incompatibility of free amines with the palladium catalyst is avoided. The cinnamylamine products are cleaved from the resin with trifluoroacetic acid under mild conditions and are converted into chromatographically separable acetamides. Our solid-phase method offers a new alternative for the synthesis of cinnamylamine derivatives, as biologically interesting compounds and useful synthetic intermediates.

Aminosilanes in organic synthesis. Hydrostannation of N,N-bis(trimethylsilyl)propargylamine. Facile and selective routes to (E)-allylic amines

The addition of tributyl tin hydride to N,N-bis(trimethylsilyl)propargylamine yielded E-1-tributylstannyl-3-prop-1-ene 2 in 90percent yield and 96percent stereochemical purity.The functional vinyl tin reagent 2 was shown to give short and selective access to primary allylic amines.The reactions of 2 with aryl and vinyl bromides in the presence of a palladium catalyst gave substituted E-allylic amines in high yields.The reaction of 2 with butyl lithium yielded E-γ-vinyl lithium from which selective access to E-allylic amines was obtained.Key words: silylamines / propargylamines / hydrostannation / vinyl tin / vinyl lithium / (E)-allylamines

A simple synthesis of primary E-allylic amines from 1-tributylstannyl-3-bis(trimethylsilyl)amino prop-1-ene

A facile and selective preparation of primary E-allylic amines is described from the readily available γ-amino vinylic tin reagent 2, either by using the direct palladium catalysed coupling of the vinyl tin moitie or via conversion to a γ-amino vinyl lithium reagent.

Phenyl substituted dipeptide amides

The invention relates to novel substituted tyrosyl alanine dipeptide amides of the formula: STR1 and the pharmaceutically acceptable acid addition salts thereof wherein R1 is hydrogen, lower alkyl, hydroxy, --OCO2 lower alkyl, lower alkoxy, --O(CH2)n -phenyl with the phenyl optionally substituted by halogen, --NO2, --CN, --NH2 or lower alkyl wherein n is 1 to 4; R2 and R3 represent lower alkyl, halogen, or lower alkoxy, or either one of R2 or R3 is hydrogen and the other is lower alkyl, lower alkoxy or halogen; R4, R5, R6, R7, R8, and R9 may be the same or different and represent hydrogen or lower alkyl; R10 is selected from the group consisting of where ALK represents alkylene, thioalkylene, oxyalkylene, having 1 to 5 carbon atoms; alkenylene and alkynylene having 2 to 4 carbon atoms; and X represents pyridyl, pyrimidinyl, 9H-fluoren-9-yl, diphenylmethyl, thienyl, carboxy, lower alkoxy carbonyl, substituted phenyl wherein the phenyl substituent is amino, hydroxy, halogen, nitro, methylenedioxy, lower alkyl, carboxy, lower alkoxycarbonyl, lower alkoxy, carboxamide, diloweralkylamino or X represents phenyl, when ALK is not alkylene; or R10 is STR2 where p and q are independently 1 to 4; or R9 and R10 together with N is STR3 where r and t are independently 1 to 4; v represents an asymmetric carbon that may be racemic or have the D or L configuration; w represents an asymmetric carbon when R7 and R8 are not the same that may be racemic or have the D or L configuration. These compounds are useful as analgesic and/or antihypertensive compounds.