Photochemical synthesis of phenanthridines: exploring fluoro and protected catechol substitution

Linsenmeier, Anna M., Williams, Craig M. and Brase, Stefan (2013) Photochemical synthesis of phenanthridines: exploring fluoro and protected catechol substitution. European Journal of Organic Chemistry, 18 3847-3856. doi:10.1002/ejoc.201300218


Author Linsenmeier, Anna M.
Williams, Craig M.
Brase, Stefan
Title Photochemical synthesis of phenanthridines: exploring fluoro and protected catechol substitution
Journal name European Journal of Organic Chemistry   Check publisher's open access policy
ISSN 1434-193X
1099-0690
Publication date 2013-05
Sub-type Article (original research)
DOI 10.1002/ejoc.201300218
Open Access Status
Volume 18
Start page 3847
End page 3856
Total pages 10
Place of publication Weinheim, Germany
Publisher Wiley - V C H Verlag
Collection year 2014
Language eng
Abstract Substituted phenanthridines, such as the natural product trispheridine, have been accessed by the practical photochemical cyclization of N-benzylanilines. Functionalities, with a focus on fluoro substituents and protected catechols, are well tolerated on both the A and C rings. The phenanthridines were accessed in good to very good yields (up to 95 %) from iodinated substrates, whereas brominated substrates performed poorly in comparison (0-48 %). Substituted phenanthridines, such as the natural product trispheridine, can be accessed by the practical photochemical cyclization of N-benzylanilines, with functionalities tolerated on both the A and C rings. The phenanthridines are accessible in good to very good yields (up to 95 %) from iodinated substrates, whereas brominated substrates perform poorly in comparison (0-48 %).
Keyword Cyclization
Fused heterocycles
Natural products
Photolysis
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2014 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 24 May 2013, 15:02:16 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences