110936-96-4

Upstream product

• 55183-44-3 4-pentynoic chloride 
• 62-53-3 aniline 
• 6089-09-4 4-pentynoic acid 
• 112404-82-7 4-pentinoyl isothiocyanate 

Downstream Products

• 1189050-88-1 3a-methyl-5-m-tolyl-3,3a-dihydropyrrolo[1,2-a]quinolin-1(2H)-one 
• 1189050-86-9 3a-methyl-5-phenyl-3,3a-dihydropyrrolo[1,2-a]quinolin-1(2H)-one 
• 1189050-87-0 3a-methyl-5-p-tolyl-3,3a-dihydropyrrolo[1,2-a]quinolin-1(2H)-one 
• 62-53-3 aniline 
• 103988-85-8 5-methyl-1-phenyl-1,3-dihydro-pyrrol-2-one 
• 1432629-43-0 tert-butyl phenyl(5-phenylpent-4-yn-1-yl)carbamate 
• 1432629-42-9 isopropyl 6-((tert-butoxycarbonyl)(phenyl)amino)hex-2-ynoate 

Relevant academic research and scientific papers

Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels-Alder reactions

Substituted 3,4-dihydro-1,8-naphthyridin-2(1H)-ones have been synthesized with the inverse electron-demand Diels-Alder reaction from 1,2,4-triazines bearing an acylamino group with a terminal alkyne side chain. Alkynes were first subjected to the Sonogashira cross-coupling reaction with aryl halides, the product of which then underwent an intramolecular inverse electrondemand Diels-Alder reaction to yield 5-aryl-3,4-dihydro-1,8-naphthyridin-2(1H)-ones by an efficient synthetic route.

Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes

A photoinitiated anti-hydropentafluorosulfanylation of terminal alkynes using SF5Cl and (TMS)3SiH as the hydrogen atom donor is reported. This transformation generates selectively (Z)-(1-alken-1-yl)pentafluoro-λ6-sulfanes

Repurposing the 3-Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification

Genome mining of microbial natural products enables chemists not only to discover the bioactive molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate-forming enzyme that adenylates a unique building block, 3-isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile natural product SF2768 produced by Streptomyces thioluteus, and this AMP-ligase was demonstrated to accept a broad range of short-chain fatty acids (SCFAs). Herein, we repurpose SfaB to catalyze amidation or thioesterification between those SCFAs and various amine or thiol nucleophiles, thereby providing an alternative enzymatic approach to prepare the corresponding amides and thioesters in vitro.

Synthesis of Exo- and Endocyclic Enamides Through Copper-Catalyzed Regioselective Intramolecular N-Halovinylation

Cross-couplings between amides and 1,2-dihaloalkenes are an efficient and straightforward way to access β-haloenamides which, in turn, can be functionalized into complex, stereodefined enamide motifs. However, the intramolecular version of these cross-couplings, leading to cyclic β-haloenamides, has not been formally studied. In this paper, we report an investigation of factors affecting the efficiency of the reaction and its selectivity between potential exo and endo cyclization products. We demonstrate that exo/endo selectivity is largely determined by ring strain, whether it arises from the size of the resulting ring or from the structure of the starting compound, but that selectivity can also be modulated by varying reaction conditions. Finally, we show that resulting β-haloenamides readily undergo transition metal-catalyzed reactions, making this sequence a viable way to access highly functionalized cyclic enamides.

Gold-catalyzed one-pot cascade construction of highly functionalized pyrrolo[1,2-a]quinolin-1(2H)-ones

(Chemical Equation Presented) An efficient protocol was developed for the synthesis of fused heterocyclic multiring compounds pyrrolo[1,2-a]quinolin-1(2H) -ones via a AuBr3/AgSbF6-catalyzed cascade transformation. Significantly, the

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.