Synthesis 2017; 49(22): 4955-4977
DOI: 10.1055/s-0036-1588586
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© Georg Thieme Verlag Stuttgart · New York

Versatile Pyrolytic Synthesis of Fused Polycyclic Heteroaromatic Compounds

EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK   Email: raa@st-and.ac.uk
,
Alasdair N. Garnett
EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews, Fife, KY16 9ST, UK   Email: raa@st-and.ac.uk
› Author Affiliations
We thank EPSRC (UK) for a studentship to A.N.G.
Further Information

Publication History

Received: 15 August 2017

Accepted after revision: 15 September 2017

Publication Date:
11 October 2017 (online)


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 pentacyclic 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.

 
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