51234-11-8

Upstream product

• 13141-38-3 2-phenylethynylaniline 
• 452962-72-0 3-iodo-2-phenyl-1-(4-toluenesulfonyl)indole 
• 948-65-2 2-phenyl-indole 

Downstream Products

• 452962-72-0 3-iodo-2-phenyl-1-(4-toluenesulfonyl)indole 
• 1175540-21-2 2-methyl-4-(1-methyl-2-phenyl-indol-3-yl)but-3-yn-2-ol 
• 53904-16-8 5,10-dihydroindeno<1,2-b>indol-10-one 
• 452962-71-9 3-iodo-1-methyl-2-phenyl-1H-indole 

Relevant academic research and scientific papers

A Versatile C–H Halogenation Strategy for Indole Derivatives under Electrochemical Catalyst- and Oxidant-Free Conditions

Halogenated indoles are essential structural motifs in bioactive natural products. Reported herein is an economical and scalable electrochemical protocol for regioselective 3C–H halogenation of indole derivatives. This strategy provides access to a host of 3-iodo-, 3-bromo-, 3-chloro-, and 3-thiocyanoindole derivatives under mild conditions using inexpensive (pseudo)halide salts as the sole reagent. The optimized conditions do not require any supplementary electrolyte salts.

Cyanine-like dyes with large bond-length alternation

Herein, the synthesis and properties of alkyne-bridged carbocations, which are analogous in structure to cyanine dyes, are reported. An alkene-bridged dye, linked at the third position of the indole, was also synthesized as a reference compound. These new carbocations are stable under ambient conditions, allowing characterization by UV/Vis and NMR (1H and 13C) spectroscopies. These techniques revealed a large degree of delocalization of the positive charge, similar to a previously reported porphyrin carbocation. The linear and nonlinear optical properties are compared with cyanine dyes and triarylmethyl cations, to investigate the effects of the bond-length alternation and the overall molecular geometry. The value of Re(γ), the real part of the third-order microscopic polarizability, of -1.3×10-33 esu for the alkyne-linked cation is comparable to that of a cyanine dye of similar length. Nondegenerate two-photon absorption spectra showed that the alkene-bridged dye exhibited characteristics of cyanines, whereas the alkyne-bridged dye is reminiscent of octupolar chromophores, such as the triarylmethyl carbocation brilliant green. Such attributes were confirmed and rationalized by quantum chemical calculations. Copyright

Scaffold-divergent synthesis of ring-fused indoles, quinolines, and quinolones via iodonium-induced reaction cascades

N-(2-Iodophenyl)imines A are readily formed from Schiff's base condensation of 2-iodoanilines with carbonyls and ketals. These imines provide useful substrates in scaffold-divergent synthesis through the attachment of an alkyne (Songashira coupling or acyl substitution of a Weinreb amide) followed by an iodonium-induced reaction cascade to give ring-fused indoles B, quinolines C, or quinolones D depending on the reaction conditions employed.

Synthesis and DNA-binding affinity studies of glycosylated intercalators designed as functional mimics of the anthracycline antibiotics

Anthracycline antibiotics such as daunomycin (Dauno) and doxorubicin (Dox) are well-known clinically used cancer chemotherapeutics, which, among other mechanisms, bind to DNA, thereby triggering a cascade of biological responses leading to cell death. However, anthracyclines are cardiotoxic, and drug resistance develops rapidly, thus limiting their clinical use. We report here the synthesis and DNA-binding affinity of a novel class of functional anthracycline mimetics consisting of an aromatic moiety linked to a carbohydrate (1-12). In the targets, the aromatic core consists of a 2-phenylbenzo[b]furan- 3-yl, 2-phenylbenzo[b]thiophen-3-yl, 1-tosyl-2-phenylindol-3-yl, or 2-phenylindol-3-yl group that is bound to one of three aminosugars (daunosamine, acosamine, or 4-amino-2,3,4,6-tetradeoxy-α-l-hexopyranoside) via a propargyl linker. The DNA binding affinity of these twelve compounds has been evaluated by using both direct and indirect fluorescence measurements. Compared to Dauno and Dox, the DNA binding affinity of these analogues is weaker. However, both aromatic and aminosugar motifs are critical to DNA binding, with more influence coming from the structural features of the aromatic portion.

Alternating lodonium-mediated reaction cascades giving indole- And quinoline-containing polycycles

A simple two-step convergent protocol gives direct access to synthetic Intermediate A from ortho-iodoanilines. Intermediate A can be treated with NIS In CH2CI2 to Induce novel lodonium mediated domino reaction cascade, which provides direct access to ring-fused Indole compounds B. Simply by changing the reaction conditions, this protocol can be directed down an alternative domino reaction cascade to give various ring fused quinoline compounds C.

Gold(III)-catalyzed annulation of 2-alkynylanilines: A mild and efficient synthesis of indoles and 3-haloindoles

Gold(III)-catalyzed annulation of 2-alkynylanilines in EtOH or EtOH-water mixtures at room temperature gives indoles derivatives in good yields. One-flask protocol for the gold-catalyzed conversion of 2-alkynylanilines to 3-bromo and 3-iodoindoles is also reported.

IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes: Direct assembly of 3-iodoindole cores

All at once! Indoles can be assembled and iodinated in a one-pot process (see scheme) from anilines and their derivatives. This metal-free addition of nitrogen compounds to alkynes is a clean reaction that is promoted by iodonium cations. Such a process p