Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds

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Aryl-aryl bond formation one century after the discovery of the Ullmann reaction.

The direct functionalization of C-H bonds in organic compounds has recently emerged as a powerful and ideal method for the formation of carbon-carbon and carbon-heteroatom bonds. This Review provides an overview of C-H bond functionalization strategies for the rapid synthesis of biologically active compounds such as natural products and pharmaceutical targets.

C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals

This Review covers recent progress on near-infrared fluorescence imaging for preclinical animal studies and clinical diagnostics and interventions.

Near-infrared fluorophores for biomedical imaging

Since the discovery of organic azides by Peter Griess more than 140 years ago, numerous syntheses of these energy-rich molecules have been developed. In more recent times in particular, completely new perspectives have been developed for their use in peptide chemistry, combinatorial chemistry, and heterocyclic synthesis. Organic azides have assumed an important position at the interface between chemistry, biology, medicine, and materials science. In this Review, the fundamental characteristics of azide chemistry and current developments are presented. The focus will be placed on cycloadditions (Huisgen reaction), aza ylide chemistry, and the synthesis of heterocycles. Further reactions such as the aza-Wittig reaction, the Sundberg rearrangement, the Staudinger ligation, the Boyer and Boyer-Aube rearrangements, the Curtius rearrangement, the Schmidt rearrangement, and the Hemetsberger rearrangement bear witness to the versatility of modern azide chemistry.

Organic Azides: An Exploding Diversity of a Unique Class of Compounds

Focused microwave irradiation of a series of halogenated nitrogen heterocycles and different kinds of nucleophiles in the presence of a catalytic amount of indium trichloride leads to the efficient and completely regioselective generation of aromatic CC and CN bonds. The method is simple, rapid, general and inexpensive, and can be performed without the use of dried solvents. Most of the synthetized compounds are new and in many cases the work-up required only filtration. Furthermore, this is the first example of the use of a Lewis acid as a catalyst for heteroarylation, vinylation and amination reactions on π-deficient heterocyclic substrates.

Lewis Acid‐Catalyzed Generation of CC and CN Bonds on π‐Deficient Heterocyclic Substrates

Efficient, multigram-scale synthesis of three 2,5-dihalobenzoquinones

Many anticancer drugs in clinical use interact with DNA through intercalation The intercalation process starts with the transfer of the intercalating molecule from an aqueous environment to the hydrophobic space between two adjacent DNA base pairs DNA intercalators are less sequence selective than minor groove binding agents, and, in contrast with them, show a preference for G–C region s This selectivity is mainly due to complementary hydrophobic or electrostatic interactions, which are due to substituents attached to the chromophore within the major or minor grooves Intoplicine is an intercalating compound that can be considered as structurally related to the ellipticines It behaves as a dual topoisomerase I and II poison at cleavage sites different to those of other known topoisomerase inhibitors Chartreusin and elsamicin A are structurally related antitum or antibiotics that were isolated from Strep- tomyces chartreusis and from an unidentified actino mycete strain, respectively Identical loops of DNA having different numbers of twists are topoisomers, that is, molecules with the same formula but different topologies, and their interconversion requires the breaking of DNA strands

DNA Intercalators and Topoisomerase Inhibitors

Advances in the Chemistry of Tetrahydroquinolines

The cyclization of all four diastereoisomers of cyclo -(Trp-Ala) to the corresponding 3,5a,6,10b,11,11a-hexahydro-2 H -pyrazino[2′,1′-5,1]pyrrolo[2,3- b ]indoles is studied from the stereochemical point of view. Epimerization of the tryptophan stereocenter during the cyclization and during acylation reactions of the N-2 atom of the tetracyclic derivatives is discussed.

J. Carlos Menéndez

Papers

Lewis Acid‐Catalyzed Generation of CC and CN Bonds on π‐Deficient Heterocyclic Substrates

Efficient, multigram-scale synthesis of three 2,5-dihalobenzoquinones

DNA Intercalators and Topoisomerase Inhibitors

Advances in the Chemistry of Tetrahydroquinolines

Stereochemical issues related to the synthesis and reactivity of pyrazino[2′,1′-5,1]pyrrolo[2,3-b]indole-1,4-diones