synthesis-antiviral-tetrahydrocarbazole-derivatives-photochemical

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

The direct functionalization of C-H bonds is an important and long standing goal in organic chemistry. Such transformations can be very powerful in order ...

Max-Planck-Institut fuer Kohlenforschung

The title compound, C(6)H(15)N(2)(+)·C(2)H(6)NO(4)S(2)(-), crystallizes as a 0.11-hydrate, (I), in the space group C2; the asymmetric unit consists of two cations (one of each enantiomer), one anion on a general position, two half anions, each with the N atom on a twofold axis, and approximately one fifth of a water molecule. The general anion departs significantly from the usual conformation: it lacks one of the typical `W'-shaped sequence of O-S-N-S-O atoms. The compound also crystallizes in the solvent-free form, (II), in the space group P2(1)/c, with one formula unit in the asymmetric unit. Both compounds form ribbons of hydrogen-bonded cation dimers parallel to the b axis. In (I), there are two independent ribbons of opposite chirality, each involving one anion on a special position, and these ribbons are connected by hydrogen bonds to the anion on a general position, resulting in a layer structure parallel to (100). In (II), the chains are connected by hydrogen bonds, and again a layer structure parallel to (100) results.

Polysulfonylamines. CXCI. The `almost' polymorphs rac-trans-2-aminocyclohexan-1-aminium di(methanesulfonyl)azanide and its 0.11-hydrate.

A Brønsted acid catalyzed C-H functionalization via Intermediate PeroxideS (CHIPS), generated photochemically, allows the oxidative coupling of indole derivatives with a variety of nitrogen nucleophiles. The reaction can be performed in one pot and requires only visible light, elemental oxygen, a Brønsted acid and a photosensitizer. The method can be applied to an efficient synthesis of some biologically active compounds.

Naeem Gulzar

Max-Planck-Institut fuer Kohlenforschung

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)