169170-37-0

Upstream product

• 52670-38-9 2-ethynylaniline 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 615-43-0 2-iodophenylamine 
• 107793-07-7 methyl 2-(2-trimethylsilyl-1-ethynyl)benzoate 
• 88-67-5 2-Iodobenzoic acid 
• 103529-16-4 2-[(trimethylsilyl)ethynyl]aniline 
• 33577-99-0 2-ethynyl-benzoic acid methyl ester 

Downstream Products

• 473932-28-4 (S)-2-[2'-(2''-acetylamino-3''-methylbutyrylamino)phenylethynyl]benzoic acid methyl ester 
• 1044518-10-6 methyl 2-[1H-indol-2-yl]benzoate 
• 40142-60-7 methyl 2-(1H-indazole-3-carbonyl)benzoate 

Relevant academic research and scientific papers

2-Amino-2′-carboxydiphenylacetylenes as β-turn mimetics. Synthesis and conformational properties

Peptide-linked 2-amino-2′ -carboxydiphenylacetylenes 1 by 1H NMR spectroscopy are shown to assume short sheet structures with distinctive CD signatures.

Acid-Promoted Bicyclization of Diaryl Alkynes: Synthesis of 2 H-Indazoles with in Situ Generated Diazonium Salt as Nitrogen Source

An unprecedented transition-metal-free tandem bicyclization of diaryl alkynes has been disclosed, which provides a streamlined access to a range of polycyclic 2H-indazoles in high to excellent yields. The salient features of this reaction include readily

Hypervalent Iodine-Mediated Intramolecular trans-Aminocarboxylation and Oxoaminocarboxylation of Alkynes: Divergent Cascade Annulations of Isocoumarins under Metal-Free Conditions

An exclusive trans-aminocarboxylation and oxoaminocarboxylation of diarylalkynes were realized through hypervalent iodine-mediated cascade annulations under metal-free conditions, leading to divergent assembly of fused or spiro polycyclic heterocycles wit

Hypervalent-Iodine-Mediated Cascade Annulation of Diarylalkynes Forming Spiro Heterocycles under Metal-Free Conditions

An unusual reaction featuring the cascade annulation of internal alkynes to afford spiro heterocycles as the products has been realized for the first time with a hypervalent iodine reagent as the only oxidant. This unprecedented process encompasses not only two sequential C-N/C-O-bond formations, but also the insertion of a carbonyl oxygen, all in one pot under metal-free conditions.

Cu(OTf)2-Catalyzed Intramolecular Radical Cascade Reactions for the Diversity-Oriented Synthesis of Quinoline-Annulated Polyheterocyclic Frameworks

Compound libraries with high levels of structural diversity and novelty could cover underexploited chemical space and thus have been highly pursued in drug discovery. Herein, we report the first Cu(OTf)2-catalyzed intramolecular radical cascade reactions

Metal-Free Synthesis of 4-Chloroisocoumarins by TMSCl-Catalyzed NCS-Induced Chlorinative Annulation of 2-Alkynylaryloate Esters

4-Chloroisocoumarins can be conveniently prepared from 2-alkynylaryloate esters via the activation of alkynes by electrophilic chlorine, generated in situ from N-chlorosuccinimide (NCS) in the presence of 10 mol % trimethylsilyl chloride (TMSCl), which leads to 6-endo-dig-selective chlorinative annulation to give the desired products in moderate to quantitative yields. The procedure employs readily available reagents and can be conveniently carried out on a wide scope of substrates under mild conditions (0 °C to rt). Furthermore, the reaction is scalable for gram-scale preparation of 4-chloroisocoumarins. Additionally, 4-bromo- and 4-iodoisocoumarins can be prepared in moderate to good yields by replacing NCS with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS), respectively.

Photophysical and theoretical studies of diphenylacetylene derivatives with restricted rotation

Diphenylacetylene derivatives containing electron-donor (amino) and electron-acceptor (ester) groups in 2,2′ or 3,2′ positions in phenyl rings were synthesized to study the effects of intramolecular charge transfer and stiffening of the conformation by in

Synthesis and incorporation into cyclic peptides of tolan amino acids and their hydrogenated congeners: Construction of an array of A-B-loop mimetics of the Cε3 domain of human IgE

The disruption of the human immunolobulin E-high affinity receptor I (IgE-FcεRI) protein-protein interaction (PPI) is a validated strategy for the development of anti asthma therapeutics. Here, we describe the synthesis of an array of conformationally constrained cyclic peptides based on an epitope of the A-B loop within the Cε3 domain of IgE. The peptides contain various tolan (i.e., 1,2-biarylethyne) amino acids and their fully and partially hydrogenated congeners as conformational constraints. Modest antagonist activity (IC50 ～660 μM) is displayed by the peptide containing a 2,2′-tolan, which is the one predicted by molecular modeling to best mimic the conformation of the native A-B loop epitope in IgE.

Copper(I) mediated intramolecular cyclization of 2-(2-amino-phenylethynyl)benzoic and [2-(2-aminophenylethynyl)phenyl]acetic acid esters: A new synthetic step towards isoindolo[2,1-a]indoles and 5H-indolo[2,1-a]isoquinolines

We describe herein parallel synthetic routes to isoindolo[2,1-a]indoles and 5H-indolo[2,1-a]isoquinolines from 2-(2-aminophenylethynyl)benzoic acid esters and [2-(2-aminophenylethynyl)phenyl]acetic acid esters, respectively.

Insight into β-hairpin stability: A structural and thermodynamic study of diastereomeric β-hairpin mimeticsy

Two diastereomers of a model β-hairpin peptide mimetic were synthesized and studied with a combination of experimental (NMR, X-ray, CD, MS, IR) and computational methods (Monte Carlo/molecular mechanics calculations). The secondary structure-stabilizing effects of hydrophobic interactions and hydrogen bonding were investigated. Comparison of the extent of folded hairpin population in non-competitive, polar aprotic, and polar protic solvents illustrates the critical role of intramolecular hydrogen bonding on hairpin stability. Investigation of 1H NMR melting curves of the diastereomeric compounds in a variety of solvents allowed an evaluation of the role of hydrophobic effects on secondary structure stabilization to be made.