We herein described an intramolecular imino Diels-Alder reaction promoted with BF(3).OEt(2)/DDQ affording substituted quinolines. Using this procedure, we prepared the chiral quinoline moiety of the uncialamycin, a new enediyne natural product.

Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl-metal species, which then rearranges selectively by careful choice of cat...

We hypothesize that iodine allergy is an immune response to iodinated self proteins produced in vivo from various iodine-containing chemicals. Since an antigenic determinant ofexperimental iodine allergy is diiodotyrosine (DIT), we designed low molecular weight DIT derivatives having provocative antigenicity without sensitizing immunogenicity, Tetraiododityrosine and hexaiodotrityrosine provoke...

We show that illumination of the chlorine dioxide-iodine-malonic acid reaction with visible light suppresses oscillations and shifts the steady state of the reaction to lower concentrations of iodide ions. In the system with starch, illumination results in a strong decrease of the steady-state concentration of the triiodidestarch complex. We suggest a simple mechanism, in which iodine atoms pro...

A highly efficient, simple and green solvent-free protocol for the preparation of poly-substituted quinolines via Friedländer hetero-annulation reaction between 2-aminoaryl ketones and carbonyl compounds in the presence of silica-supported P2O5 (P2O5 / SiO2) is described. In this method, the title compounds are obtained in high to exc...

The reduction of unprotected indoles and quinolines is described using water as a hydrogen source. The method is based on the application of a RANEY® type Ni-Al alloy in an aqueous medium. During the reaction the Al content of the alloy, used as reductants, reacts with water in situ providing hydrogen and a RANEY® Ni catalyst, thus the alloy serves as a hydrogen generator as well as a hydrogena...

A Ni-catalyzed asymmetric reductive cross-coupling of heteroaryl iodides and α-chloronitriles has been developed. This method furnishes enantioenriched α,α-disubstituted nitriles from simple organohalide building blocks. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, quinolines, thiophenes, and piperidines. The reaction proceeds under mild ...

A new bicyclization strategy has been established, allowing a flexible and practical approach to 33 examples of pyrazolo[3,4-c]quinolines from low-cost and readily accessible triethylammonium thiolates with hydrazines. Notably, the features of this work include broad functional group compatibility, mild reaction conditions and good reaction yields.

Trivalent iodine compounds have found widespread applications as oxidants and electrophilic group-transfer agents for organic synthesis. Over the last several years, our group has developed new reactions synthetic methods of a class stable trivalent known benziodoxol(on)es. This article summarizes studies on (1) palladium-catalyzed transformations ethynylbenziodoxol(on)es beyond alkynyl transfe...

A new synthetic route to indeno[1,2-b]quinolines via reactions of o-propargylbenzaldehydes with N-aryl amines based on an intramolecular aza-Diels-Alder (Povarov) reaction has been developed. This method offers several advantages such as no requirement for an oxidant, high efficiency, and a wide reaction scope.