Novel syntheses of functionalized indoles, quinolines, and isoquinolines

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Project Summary The objective of this proposal is to develop innovative new synthetic methodologies for the synthesis of indole, quinoline, and isoquinoline scaffolds. It is anticipated that the methodologies proposed would furnish simple, mild, and flexible synthetic routes to an array of functionalized indoles, N-hydroxy, N-alkoxyindoles, quinolines, quinoline N- oxides, isoquinolines, and isoquinoline N-oxides. The research is of relevance to synthetic, medicinal, and pharmaceutical chemists and scientists in related fields both in industry and academia. The proposed work is divided into four sections each describing a novel methodology for expedient synthesis of functionalized heterocyclic compounds. In the first section, palladium catalyzed, base and CO mediated, indole/quinoline/isoquinoline syntheses will be presented together with a short synthesis of pyrroloquinolines alkaloids. The second section expands on the first section into the synthesis of 4-arylquinolines and applications in pyridoacridine alkaloid synthesis. Photochemically induced, palladium catalyzed, reactions will be examined in the third section, with the expectation of the development of complementary, mild, methodologies. Finally, base-mediated reactions to N-oxygenated ring systems in the absence of a catalyst will be studied in the fourth section. The participants, other that the PI, on the project will be one undergraduate student (3 months during each summer for three years) and two graduate students (full time for 3 years). The students will be trained in state of the art organic and organometallic synthesis including experimental design and execution, product purification, and product identification and characterization by spectroscopical means (NMR, IR, HRMS, UV-VIS, etc.).