The Bull-Hutchings-Quayle (BHQ) reaction is a novel method for the synthesis of 1-(bromo/chloro)napthalenes from 2-allyphenyl-2’,2’,2’-tri(bromo/chloro)acetates. The reaction is also known as Atom Transfer Radical Cyclisation-Benzannulation (ATRC-Benzannulation). The ATRC-Benzannulation of structurally diverse 2-(cyclohex-1-en-1-ylmethyl)phenyl 2’,2’,2’-trichloroacetates in the presence of 1,3bis-(2,6diisopropylphenyl)imidazolium copper(I) chloride [“Nolan NHC-CuCl”] complexes, using microwave or thermolytic methods, afford a range of 9-chloro-1,2,3,4-tetrahydroanthracenes. Efficient ATRC-Benzannulation has been restricted to microwave conditions so a thermolytic method has been developed as an alternative. Application of BHQ methodology toward the synthesis of the core structure of lactonamycin are reported. Stille, Suzuki and Sonogashira cross-coupling methods were used for the synthesis of diene precursors of a lactonamycin analogue. [4+2] Diels-Alder cycloadditions have been investigated with the diene precursors and various dienophiles. 1-Chloroquinone has been displaced with para-methoxyphenol to generate 1-para-methoxyquinone. CAN mediated oxidation of 1-para-methoxyquinone has yielded 1-hydroxyquinone.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:606964 |
| Date | January 2013 |
| Creators | Hussain, Jakir |
| Contributors | Quayle, Peter |
| Publisher | University of Manchester |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | https://www.research.manchester.ac.uk/portal/en/theses/approaches-toward-the-synthesis-of-lactonamycin-utilising-a-new-benzannulation-reaction(1157cbe4-21f4-4d9e-a10d-cf20518eb30b).html |
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