452962-72-0Relevant academic research and scientific papers
IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes: Direct assembly of 3-iodoindole cores
Barluenga, Jose,Trincado, Monica,Rubio, Eduardo,Gonzalez, Jose M.
, p. 2406 - 2409 (2003)
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
Synthesis and Stabilities of 3-Borylated Indoles
Al-Saedy, Muhannad A. E.,Harrity, Joseph P. A.
supporting information, p. 1674 - 1676 (2016/07/06)
We report herein that 3-pinacol boronic esters undergo facile protodeborylation in the presence of palladium catalysts and base, and this contributes significantly to the generation of nonborylated indole byproducts in the B2Pin2-med
A concise approach for the synthesis of 3-iodoindoles and 3-iodobenzo[b]furans via Ph3P-catalyzed iodocyclization
Li, Yin-Long,Li, Jian,Yu, Sheng-Nan,Wang, Ji-Bo,Yu, Yan-Min,Deng, Jun
, p. 8271 - 8277 (2015/10/05)
A variety of 3-iodoindole and 3-iodobenzo[b]furan derivatives were conveniently prepared from the corresponding 2-alkynylanilines and 2-alkynylphenols through Ph3P-catalyzed iodocyclization in the presence of N-iodosuccinimide (NIS). This proto
Silver-catalyzed cascade cyclization-stannylation of o-alkynylaniline derivatives with 2-tributylstannylfuran: An efficient synthesis of (3-indolyl)stannanes
Liu, Jun,Xie, Xin,Liu, Yuanhong
supporting information, p. 11794 - 11796 (2013/12/04)
A straightforward synthesis of (3-indolyl)stannanes through silver-catalyzed cyclization-stannylation of N-electron-withdrawing group-substituted o-alkynylanilines in the presence of 2-tributylstannylfuran is developed. This method offers several advantages such as no requirement of additional ligands, high efficiency and a wide reaction scope.
Synthesis and DNA-binding affinity studies of glycosylated intercalators designed as functional mimics of the anthracycline antibiotics
Shi, Wei,Coleman, Robert S.,Lowary, Todd L.
supporting information; experimental part, p. 3709 - 3722 (2009/10/23)
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.
A simple, two-step synthesis of 3-iodoindoles
Amjad, Muhammad,Knight, David W.
, p. 539 - 541 (2007/10/03)
2-Halo-anilines, protected as the corresponding sulfonamides or carbamates, can be converted very efficiently into 3-iodoindoles by sequential Sonogashira coupling with a 1-alkyne and 5-endo-dig iodocyclisation. Azaindoles can also be obtained using this methodology.
Synthesis of fluoren-9-ones by the palladium-catalyzed cyclocarbonylation of o-halobiaryls
Campo, Marino A.,Larock, Richard C.
, p. 5616 - 5620 (2007/10/03)
The synthesis of various substituted fluoren-9-ones has been accomplished by the palladium-catalyzed cyclocarbonylation of o-halobiaryls. The cyclocarbonylation of 4′-substituted 2-iodobiphenyls produces very high yields of 2-substituted fluoren-9-ones bearing either electron-donating or electron-withdrawing substituents. 3′-Substituted 2-iodobiphenyls afford 3-substituted fluoren-9-ones in excellent yields with good regioselectivity. This chemistry has been successfully extended to polycyclic fluorenones and fluorenones containing fused isoquinoline, indole, pyrrole, thiophene, benzothiophene, and benzofuran rings.
