112404-94-1

Upstream product

• 112404-82-7 4-pentinoyl isothiocyanate 
• 100-46-9 benzylamine 
• 55183-44-3 4-pentynoic chloride 
• 6089-09-4 4-pentynoic acid 
• 132178-37-1 2,5-dioxopyrrolidin-1-yl pent-4-ynoate 

Downstream Products

• 22568-12-3 1-benzyl-5-methylene-pyrrolidin-2-one 
• 143427-45-6 N-(4-methylbenzyl)-4-pentyn-1-amine 
• 1337864-04-6 N-benzyl-3-{2-methoxy-5-[hydroxyl-bis(4-methoxyphenyl)methyl]phenyl}-4-pentynoic amide 
• 57171-01-4 5-benzoyl-1-benzylpyrrolidin-2-one 

Relevant academic research and scientific papers

Diethylzinc-Mediated Radical 1,2-Addition of Alkenes and Alkynes

A novel diethylzinc-mediated radical 1,2-addition of perfluoroalkyl iodides to unactivated alkenes and alkynes is presented, which demonstrates a novel way to generate an ethyl difluoroacetate radical. This method is highly efficient and gives full conversions of the substrates, high yields of the products, and negligible byproducts and requires no column chromatography purifications. The mild conditions enable this protocol to exhibit excellent functional group compatibility.

A diastereocontrolled route to 10-arylpyrrolo[1,2-b ]isoquinolines

The diastereocontrolled preparation of a series of 10-aryl-substituted pyrroloisoquinolines is achieved through a synthetic design that involves two key cyclization steps. First, the iodine(III)-mediated reaction of a series of N-benzylpentynamides leads to the generation of the 5-aroylpyrrolidinone skeletons. Finally, after reduction of the generated ketone group into the corresponding carbinol, the effect of a number of different acidic conditions was studied to assist the second cyclization step that occurs through an aromatic electrophilic substitution process. The study of the stereochemical course of this step led us to conclude that it takes place through a S N1 mechanism with very high (>95% anti) diastereocontrol.

Synthesis of acyclic α,β-unsaturated ketones via Pd(II)-catalyzed intermolecular reaction of alkynamides and alkenes

We report an intermolecular oxidative coupling of alkynamides and terminal alkenes to synthesize E-α,β-unsaturated ketones under very mild conditions using catalytic Pd(II) and an oxidant. An 17O isotope labeling experiment implicates a cyclic

RADIOLABELLING METHODS

The invention relates to radiodiagnostic and radiotherapeutic agents, including biologically active vectors labelled with radionuclides. It further relates to methods and reagents labelling a vector such as a peptide comprising reaction of a compound of f

Catalytic one-pot synthesis of cyclic amidines by virtue of tandem reactions involving intramolecular hydroamination under mild conditions

A new synthetic methodology for the generation of cyclic amidines has been developed by the reaction of 1,n-aminoalkynes with electron-deficient azides using a ruthenium catalyst at ambient temperature. The reaction proceeds most likely via a tandem sequence of intramolecular hydroamination of aminoalkynes, cycloaddition of azides with the resulting enamines, and rearrangement of triazoline intermediates. It demonstrates, as the proof-of-principle, that an equilibria cascade sequence can be favorably driven by an irreversible step, thus enabling a facile one-pot synthetic route to deliver molecular complexity under unprecedented mild conditions without relying on the traditional linear approaches. Copyright

Dihydropyrromethenones by Pd(0)-Mediated Coupling of Iodopyrroles and Acetylenic Amides. Synthesis of the A,B-Ring Segment of Phytochrome

Dihydropyrromethenone derivative 32b, which constitutes the A,B-ring segment of phytochrome (6), has been prepared in enantiomerically pure form beginning with acetylenic amide 47b and iodopyrrole 27. The key steps involved the TBAF-catalyzed 5-exo-dig cyclization of the acetylenic pyrrole 48b, followed by thia-Mitsunobu inversion of the resulting alcohol derivative 31b.

Toward the synthesis of biologically important chlorins, isobacteriochlorins, and corrins. Cyclic enamides from acetylenic amides

Cyclic enamides 1 of a type useful in the synthesis of naturally occurring chlorins, isobacteriochlorins, and corrins have been prepared by a process involving 5-exo-dig cyclization of the appropriate acetylenic amides 11. The desired cyclization is catalyzed by either n-Bu4NF or LiAl-(NHBn)4.

SELECTIVITY OF NUCLEOPHILIC ADDITION TO AND SUBSTITUTION AT ISOTHIOCYANATOCARBONYL GROUP. REACTIONS OF 4-PENTINOYL- AND 2-(2-PROPINYL)-4-PENTINOYL ISOTHIOCYANATE WITH AMINES AND METHANOL

4-Pentinoyl isothiocyanate reacts with primary and secondary amines by either nucleophilic addition to N=C=S group to yield the corresponding thioureas, or a nucleophilic substitution at the carbonyl group to give 4-pentinoic acid amides.The less nucleophilic diphenylamine reacts selectively to afford the product of nucleophilic addition only. 2-(2-Propinyl)-4-pentinoyl isothiocyanate, having a sterically hindered carbonyl group, furnished with primary amines a mixture of amides and thioureas, whereas the bulkier secondary amines react selectively to form thioureasonly.Both isothiocyanates afford with methanol as a nucleophile axclusively the corresponding O-methyl monothiocarbamates.