91406-85-8

Upstream product

• 123-72-8 butyraldehyde 
• 536-74-3 phenylacetylene 
• 100-46-9 benzylamine 
• 56249-61-7 N-butylidenebenzylamine 
• 93794-78-6 N-butylidenebenzylamine 

Downstream Products

• 1311377-69-1 1,4-dibenzyl-3-(4-methoxyphenyl)-5-propyl-1H-imidazol-2(3H)-one 
• 1569267-41-9 3-benzyl-1-(4-methoxyphenyl)-6-phenyl-4-propyl-3,4-dihydropyrimidin-2(1H)-one 
• 1311377-70-4 1,4-dibenzyl-3-(4-fluorophenyl)-5-propyl-1H-imidazol-2(3H)-one 
• 1569267-42-0 3-benzyl-1-(4-fluorophenyl)-6-phenyl-4-propyl-3,4-dihydropyrimidin-2(1H)-one 
• 1311377-68-0 1,4-dibenzyl-3-phenyl-5-propyl-1H-imidazol-2(3H)-one 
• 1569267-40-8 3-benzyl-1,6-diphenyl-4-propyl-3,4-dihydropyrimidin-2(1H)-one 
• 1311377-60-2 1-benzyl-3-phenyl-1-(1-phenylhex-1-yn-3-yl)urea 
• 1262680-06-7 C₃₀H₃₉N₃O₄ 

Relevant academic research and scientific papers

Activation of primary amines by copper(i)-based lewis acid promoters in the solventless synthesis of secondary propargylamines

Primary amines are activated by copper(I)-based Lewis acid promoters in an A 3 -coupling one-pot solventless reaction with aldehydes and phenylacetylene for the synthesis of secondary propargylamines. The reaction is promoted by a CuSO 4 /NaI system, a practical precursor of the in situ generated effective CuI/I 2 system, that worked well, but only in a restricted number of examples. Substitution of I 2 with CeCl 3 ·7H 2 O in a one-pot two-step reaction provided good yields and a wider applicability, with the added value given by a safer procedure.

Copper-Catalyzed Reaction of Secondary Propargylamines with Ethyl Buta-2,3-dienoate for the Synthesis of 1,6-Dihydropyridines

A copper(I) bromide-catalyzed reaction of A3-coupling-derived propargylamines with ethyl buta-2,3-dienoate for the fast assembly of a 1,6-dihydropyridine core is described. The developed protocol was tested on a variety of secondary propargylamines and the possibility of a one-pot synthesis of 1,6-dihydropyridine through the A3-coupling and subsequent ethyl buta-2,3-dienoate incorporation was investigated.

Base-Mediated Direct Transformation of N-Propargylamines into 2,3,5-Trisubstituted 1 H-Pyrroles

An efficient and base-mediated intramolecular cyclization of N-propargylamines for the synthesis of structurally diversified pyrroles in high yield has been described. The developed methodology is broadly applicable and is tolerated by a variety of functional groups. Key intermediates of natural product discoipyrrole C as well as HMG-CoA-reductase inhibitor have been successfully synthesized using developed chemistry. The proposed mechanism was supported by control experiments.

Base-Mediated Direct Transformation of N-Propargylamines into 2,3,5-Trisubstituted 1 H-Pyrroles

An efficient and base-mediated intramolecular cyclization of N-propargylamines for the synthesis of structurally diversified pyrroles in high yield has been described. The developed methodology is broadly applicable and is tolerated by a variety of functional groups. Key intermediates of natural product discoipyrrole C as well as HMG-CoA-reductase inhibitor have been successfully synthesized using developed chemistry. The proposed mechanism was supported by control experiments.

Diversity-oriented synthesis of 1,3-benzodiazepines

A concise assembly of the 1,3-benzodiazepine core from A3-coupling-derived propargylamines and ortho-bromophenylisocyanates is described. The developed synthetic sequence involves the addition of propargylamine to isocyanate followed by palladium-catalyzed intramolecular alkyne hydroarylation that could be accomplished in a stepwise or one-pot manner.

Synthesis of Thiazolidine-2-thiones through a One-Pot A3-Coupling–Carbon Disulfide Incorporation Process

A copper-catalyzed two-step one-pot procedure for the synthesis of thiazolidine-2-thiones has been developed. The process involves a three-component coupling of an alkyne, an aldehyde, and an amine (A3-coupling) followed by trapping the resulting propargylamine with carbon disulfide and subsequent cyclization.

Tuning the reactivity of isocyano group: Synthesis of imidazoles and imidazoliums from propargylamines and isonitriles in the presence of multiple catalysts

The reaction of propargyl amines with tert-butylisonitrile in the presence of a catalytic amount of both Yb(OTf)3 and AgOTf afforded imidazoles, whereas the same reaction with primary and secondary alkylisonitriles, as well as arylisonitriles, in the presence of three metal salts [Yb(OTf)3/AgOTf/KOTf] resulted in the 1,3,4,5-tetrasubstituted imidazoliums in excellent yields. Both chiral amines and chiral isonitriles can be used to provide corresponding chiral heterocycles without racemization. In this multiple catalytic system, Yb(OTf)3 catalyzed the insertion of isonitriles to the N-H bond of amines, AgOTf catalyzed the 5-exo-dig cyclization of the resulting amidine nitrogen to the tethered triple bond, and KOTf promoted the salt metathesis, thus providing at the same time the counterion to the imidazolium. Against common knowledge, the isocyano group acted in these reactions as a polarized triple bond instead of conventional carbene-like function.

Nano-size ZnS: A novel, efficient and recyclable catalyst for A 3-coupling reaction of propargylamines

Nano-size ZnS was prepared by a simple, economic and elegant chemical bath deposition technique and characterized by using SEM, TEM, XRD, and EDAX techniques. Prepared nano-size ZnS was found to be highly efficient novel heterogeneous catalyst for A3-coupling reaction of Propargylamines (4a-4l) using various aldehydes, amines and terminal alkyne groups through CH activation. The catalyst was recycled more than eight consecutive cycles and reused in the subsequent reactions without any loss in its activity. The developed protocol offers efficient synthesis of diverse propargylamines without using co-catalyst and any other activator, high catalytic activity and short reaction times were obtained when compared to other metal ion and/or metal oxide catalysts.

One-pot, three-step copper-catalyzed five-/four-component reaction constructs polysubstituted oxa(thia)zolidin-2-imines

A novel one-pot synthesis of polysubstituted oxa(thia)zolidin-2-imines has been developed. It employs A3-coupling of aldehyde and amine with alkyne to form propargyl amine, which on (thio)amidation with iso(thio)cyanate produces N-propargyl(thio)urea, and a cyclization reaction. A 5-exo-dig iodocyclization of N-propargylurea constructs 5-iodomethyleneoxazolidin-2-imine, while cycloisomerization of the thio analogue provides 5-methylenethiazolidin- 2-imine. In this process, CuI catalysis has been found to be crucial, and the cyclization occurs through oxygen/sulfur (not nitrogen) nucleophilic attack to alkyne. Georg Thieme Verlag Stuttgart · New York.

Efficient microwave-assisted synthesis of secondary alkylproparglamines by using A3-coupling with primary aliphatic amines

(Chemical Equation Presented) Three-component coupling reaction: An efficient, microwave-assisted, CuIcatalysed A3-coupling reaction with primary aliphatic amines that gives access to secondary propargylamines is described (see schem