Chemical Structure Data File for T.V. Hughes's dissertation, "Part 1. Synthetic approaches to indole/imidazole marine alkaloids. Part 2. 1-cyanobenzotriazole as a cyanating agent. Part 3. Synthesis of potential molecular rectifiers"

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This sdf file supports the research found in Hughes' dissertation. Its abstract states: "This dissertation consists of four chapters. The first chapter details the progress toward a total synthesis of securine A (1). Securine A is an indole/imidazole containing marine alkaloid which contains a 2,3-disubstituted indole ring and a 4,5-disubstituted imidazole ring with a 12-membered lactam connecting the two. The approach into the securine A ring system utilized the opening of a pyrano[3,4-b]indol-3-one ring system with a modified histamine derivative. Efforts in the synthesis of securine A were not successful, but the synthesis of a similar analogue, compound 53, which contained a 13-membered ring was achieved.Chapter two deals with the total synthesis of the indole/maleimide/imidazole containing marine alkaloids: the didemnimides A–D (84– 87). The total syntheses of didemnimide A–D were successful and utilized a base catalyzed condensation reaction of methyl indolyl-3-glyoxylate (102) and 1-trityl-4-imidazoleacetamide (104).Chapter three details a new and convenient synthesis of 1-cyanobenzotriazole (123) and efforts to use it as a source of +CN in carbon-carbon forming reactions. The synthesis is safer than previously reported methods and allows for 123 to be made in multi-gram scale rather inexpensively. It was demonstrated that 1-cyanobenzotriazole (123) is a good source of +CN in carbon-carbon forming reactions by reacting with a variety of sp3, Sp 2, and sp carbanions.Chapter four details a new synthesis of hexadecylquinolinium tricyanoquinodimethanide (171) which has been shown to be a molecular rectifier. In search of additional molecular rectifiers, this new methodology was applied to the synthesis of Z-β-(N-n-hexadecyl-2-benzothiazolium)-α-cyano-4-styryldicyanomethanide (181) as well as its selenium and tellurium analogues 190 and 200; respectively. Additionally, the synthesis of other T-D+-π-A- types of molecules was explored in search for other molecular rectifiers. However, of all the compounds synthesized herein, only 171 has been shown to rectify."
This Structure Data File (sdf) is associated with the dissertation by T.V. Hughes ( It was generated by the University of Alabama Libraries. The .sdf file is licensed under a Creative Commons Attribution 4.0 International License (