Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/66424
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Type: | Journal article |
Title: | Fused pyrazino [2,3-b]indolizine and indolizino[2,3-b]quioxaline derivatives; synthesis, structures and properties |
Author: | Bloch, W. Derwent - Smith, S. Issa, F. Morris, J. Rendina, L. Sumby, C. |
Citation: | Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2011; 67(48):9368-9375 |
Publisher: | Pergamon-Elsevier Science Ltd |
Issue Date: | 2011 |
ISSN: | 0040-4020 1464-5416 |
Statement of Responsibility: | Witold M. Bloch, Stephanie M. Derwent-Smith, Fatiah Issa, Jonathan C. Morris, Louis M. Rendina and Christopher J. Sumby |
Abstract: | The synthesis of six new compounds incorporating either a pyrazino[2,3-b]indolizine or indolizino[2,3-b]quinoxaline core are reported in good yield (58-87%). The intermediates for the key cyclization reaction for one set of compounds (5a-c), with a sterically demanding 3,5-dimethylpyrazole group in the 5-position of the core, were found to be mono-substituted. These intermediates could be isolated and cyclized by heating under acid-catalyzed conditions. To further demonstrate the versatility of the chemistry, compounds 6a-c were synthesized in 58-68% yields. Compounds 5a-c are non-planar in solution and the solid-state, while 6a-c have close to planar conformations, pointing to weak hydrogen bonds between the acidic C-Hs and the adjacent azine nitrogen atoms. The cytotoxicity of the six newly synthesized and three previously prepared compounds was assessed against a human glioblastoma multiforme cell line. © 2011 Elsevier Ltd. All rights reserved. |
Keywords: | Fused Heterocycles Synthesis Organic dyes X-ray crystallography Biological Activity |
Rights: | Copyright Elsevier 2011 |
DOI: | 10.1016/j.tet.2011.09.133 |
Grant ID: | http://purl.org/au-research/grants/arc/DP0773011 http://purl.org/au-research/grants/arc/DP0770653 |
Description (link): | http://www.journals.elsevier.com/tetrahedron/ |
Published version: | http://dx.doi.org/10.1016/j.tet.2011.09.133 |
Appears in Collections: | Aurora harvest Environment Institute publications IPAS publications |
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hdl_66424.pdf | Accepted version | 598.3 kB | Adobe PDF | View/Open |
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