Versatile pyrolytic synthesis of fused polycyclic heteroaromatic compounds
Abstract
Thirty-six new stabilised phosphonium ylides designed to undergo thermal loss of Ph3PO and radical domino cyclisation have been prepared and are generally found to undergo the desired reaction under flash vacuum pyrolysis conditions at 850 °C. A wide range of tetra- and penta-cyclic fused ring heterocycles, many previously unknown, are thus formed in moderate to high yield in a single step. By using suitably substituted starting materials, substituents such as CH3 and Cl can be installed at various positions in the products. The method has also been demonstrated in a combinatorial mode to generate a small library of twelve fused ring heterocycles in a single pyrolysis.
Citation
Aitken , R A & Garnett , A N 2017 , ' Versatile pyrolytic synthesis of fused polycyclic heteroaromatic compounds ' , Synthesis , vol. 49 , no. 22 , pp. 4955-4977 . https://doi.org/10.1055/s-0036-1588586
Publication
Synthesis
Status
Peer reviewed
ISSN
0039-7881Type
Journal article
Rights
© 2017, Georg Thieme Verlag. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1055/s-0036-1588586
Description
The authors thank EPSRC (UK) for a studentship to ANG.Collections
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