85375-43-5

Upstream product

• 10229-11-5 4-phenyl-but-3-yn-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 591-50-4 iodobenzene 
• 161040-05-7 N-(but-3-yn-1-yl)-4-methylbenzenesulfonamide 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 98-80-6 phenylboronic acid 
• 536-74-3 phenylacetylene 
• 87639-40-5 4-phenyl-3-butyn-1-yl trifluoromethanesulfonate 

Downstream Products

• 124943-85-7 2-Ethoxy-3-((E)-4-phenyl-but-3-enyl)-azepane-1-carboxylic acid tert-butyl ester 
• 124943-85-7 2-Ethoxy-3-((Z)-4-phenyl-but-3-enyl)-azepane-1-carboxylic acid tert-butyl ester 
• 124943-73-3 2-Oxo-3-((E)-4-phenyl-but-3-enyl)-azepane-1-carboxylic acid tert-butyl ester 
• 124943-75-5 2-Oxo-3-((Z)-4-phenyl-but-3-enyl)-azepane-1-carboxylic acid tert-butyl ester 
• 124944-01-0 (3R*,2aS*,9aS*,9bS*)-5a-Aza-2,2a,3,5,6,7,8,9,9a,9b-decahydro-5-oxo-4-oxa-3-phenyl-1H-benzazulene 
• 124944-01-0 (9aR*,3S*,2aS*,9bS*)-5a-Aza-2,2a,3,5,6,7,8,9,9a,9b-decahydro-5-oxo-4-oxa-3-phenyl-1H-benzazulene 
• 124943-56-2 3-((E)-4-Phenyl-but-3-enyl)-azepan-2-one 
• 124943-58-4 ((Z)-4-Phenyl-3-butynyl)hexahydro-2H-azepin-2-one 
• 124943-84-6 2-Ethoxy-3-(4-phenyl-but-3-ynyl)-azepane-1-carboxylic acid tert-butyl ester 
• 124991-88-4 2-Oxo-3-(4-phenyl-but-3-ynyl)-azepane-1-carboxylic acid tert-butyl ester 
• 124944-08-7 C₁₇H₁₉NO₄ 
• 124943-97-1 (9aR*,9bS*)-5a-Aza-2,5,6,7,8,9,9a,9b-octahydro-5-oxo-4-oxa-3-phenyl-1H-benzazulene 
• 124943-55-1 3-(4-Phenyl-but-3-ynyl)-azepan-2-one 
• 3042-22-6 2-phenyl-1H-pyrrole 

Relevant academic research and scientific papers

Palladium-Catalyzed Synthesis of Tricyclic Indoles via a N-S Bond Cleavage Strategy

In palladium/norbornene (Pd/NBE) chemistry, the "ortho effect"has been proven to be a key factor in the process of β-carbon elimination to extrude NBE. Herein, we found that the o-iodoaniline protected by a p-methoxybenzenesulfonyl group can recover the "

Modification of the 4-phenylbutyl side chain of potent 3-benzazepine-based GluN2B receptor antagonists

Excitotoxicity driven by overactivation of NMDA receptors represents a major mechanism of acute and chronic neurological and neurodegenerative disorders. Negative allosteric modulators interacting with the ifenprodil binding site of the NMDA receptor are able to interrupt this ongoing neurodamaging process. Starting from the potent 3-benzazepine-1,7-diol 4a novel NMDA receptor antagonists were designed by modification of the N-(4-phenylbutyl) side chain. With respect to developing novel fluorinated PET tracers, regioisomeric fluoroethoxy derivatives 11, 12, 14, and 15 were synthesized. Analogs 19 and 20 with various heteroaryl moieties at the end of the N-side chain were prepared by Sonogashira reaction and nucleophilic substitution. The fluoroethyl triazole 37 was obtained by 1,3-dipolar cycloaddition. In several new ligands, the flexibility of the (hetero)arylbutyl side chain was restricted by incorporation of a triple bond. The affinity towards the ifenprodil binding site was tested in an established competition assay using [3H]ifenprodil as radioligand. Introduction of a fluoroethoxy moiety at the terminal phenyl ring, replacement of the terminal phenyl ring by a heteroaryl ring and incorporation of a triple bond into the butyl spacer led to considerable reduction of GluN2B affinity. The phenol 15 (Ki = 193 nM) bearing a p-fluoroethoxy moiety at the terminal phenyl ring represents the most promising GluN2B ligand of this series of compounds. With exception of 15 showing moderate σ2 affinity (Ki = 79 nM), the interaction of synthesized 3-benzazepines towards the PCP binding site of the NMDA receptor, σ1 and σ2 receptors was rather low (Ki > 100 nM).

External Oxidant-Free Oxidative Tandem Cyclization: NaI-Catalyzed Thiolation for the Synthesis of 3-Thiosubstituted Pyrroles

A simple method for the synthesis of 3-thiosubstituted pyrroles from homopropargylic amines and thiosulfonates via a tandem sulfenylation/cyclization has been developed. The thiosulfonates are used both as substrates and oxidants in this transformation. This procedure exhibits good functional group tolerance and a series of 3-thiosubstituted pyrrole derivatives was obtained in moderate to good yields. (Figure presented.).

Tert-Butyl Nitrite Promoted Oxidative Intermolecular Sulfonamination of Alkynes to Synthesize Substituted Sulfonyl Pyrroles from the Alkynylamines and Sulfinic Acids

tert-Butyl nitrite promoted oxidative intermolecular sulfonamination of alkynes to synthesize substituted sulfonyl pyrroles from the alkynylamines and sulfinic acids via tandem addition/cyclization was developed. This reaction is performed well by employing tert-butyl nitrite as the oxidant, and various substituted sulfonyl pyrroles are formed in moderate to good yields with no requirement of metal catalysis.

Cu-Catalyzed Tandem Aerobic Oxidative Cyclization for the Synthesis of 3,3′-Bipyrroles from the Homopropargylic Amines

A Cu-catalyzed method for the synthesis of 3,3′-bipyrroles from homopropargylic amines through tandem aerobic oxidative cyclization involving the formation of C-C bond has been developed. The features of this reaction are a small number of Cu catalysis and simple starting substrates. Moreover, this procedure exhibits good functional group tolerance and a series of 3,3′-bipyrroles derivatives are obtained in moderate to good yields.

Regioselective Amine–Borane Cyclization: Towards the Synthesis of 1,2-BN-3-Cyclohexene by Copper-Assisted Triazole/Gold Catalysis

The combination of triazole/gold (TA-Au) and Cu(OTf)2is identified as the optimal catalytic system for promoting intramolecular hydroboration for the synthesis of a six-membered cyclic amine–borane. Excellent yields (up to 95 %) and regioselectivities (5-exo vs. 6-endo) were achieved through catalyst control and sequential dilution. Good functional-group tolerance was attained, thus allowing the preparation of highly functionalized cyclic amine–borane substrates, which could not be achieved using other methods. Deuterium-labeling studies support the involvement of a hydride addition to a gold-activated alkyne with subsequent C?B bond formation.

Palladium(II)-Catalyzed Regioselective syn-Hydroarylation of Disubstituted Alkynes Using a Removable Directing Group

A palladium(II)-catalyzed regioselective syn-hydroarylation reaction of homopropargyl amines has been developed, wherein selectivity is controlled by a cleavable bidentate directing group. Under the optimized reaction conditions, both dialkyl and alkylaryl alkyne substrates were found to undergo hydroarylation with high selectivity. The products of this reaction contain a 4,4-disubstituted homoallylic amine motif that is commonly seen in drug molecules and other bioactive compounds.

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

Pd-catalysed C-C bond formation is an essential tool within the pharmaceutical and agrochemical industries. Many of these reactions rely heavily on polar aprotic solvents; however, despite their utility, these solvents are incompatible with the drive towards more sustainable chemical synthesis. Herein, we describe the scope and limitations of an alternative to DMF derived from renewable sources (Cyrene) in Sonogashira cross-coupling and Cacchi-type annulations.

Cu-catalyzed arylcarbocyclization of alkynes with diaryliodonium salts through C-c bond formation on inert C(sp3)-H bond

Copper-catalyzed arylcarbocyclization reaction of alkynes was realized with diaryliodonium salts through C-C bond formation on an inert C(sp3)-H bond. This method provides an efficient cyclization of alkyl alkynes to generate carbocycles with good step-economy. Theoretical study revealed an interesting Cu-catalyzed concerted pathway of the C-C bond formation.

Fused ring aziridines as a facile entry into triazole fused tricyclic and bicyclic heterocycles

The intramolecular dipolar cycloaddition of an azide with an alkyne has provided a useful entry into triazole fused tricyclic heterocycles containing both the triazole ring and the oxazolidin-2-one ring system. The requisite azido-alkynes have been prepared via a two-step sequence from fused ring aziridines. A series of 6-12 membered rings containing both the oxazolidinone and triazole rings have been prepared. These ring systems have been designed as conformationally restrained analogs of RNA-binding oxazolidinones. The Royal Society of Chemistry 2012.