872998-62-4Relevant academic research and scientific papers
Radical reactions with 3H-quinazolin-4-ones: Synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin
Bowman, W. Russell,Elsegood, Mark R. J.,Stein, Tobias,Weaver, George W.
, p. 103 - 113 (2008/03/14)
Alkyl, aryl, heteroaryl and acyl radicals have been cyclised onto the 2-position of 3H-quinazolin-4-one. The side chains containing the radical precursors were attached to the nitrogen atom in the 3-position. The cyclisations take place by aromatic homolytic substitution hence retain the aromaticity of the 3H-quinazolin-4-one ring. The highest yields were obtained using hexamethylditin to facilitate cyclisation rather than reduction without cyclisation. The alkaloids deoxyvasicinone 2, mackinazolinone 3, tryptanthrin 4, luotonin A 5 and rutaecarpine 8 were synthesised by radical cyclisation onto 3H-quinazolin-4-one. This journal is The Royal Society of Chemistry.
Total synthesis of luotonin and a small library of AB-ring substituted analogues by cascade radical annulation of isonitriles
Tangirala, Raghuraman,Antony, Smitha,Agama, Keli,Pommier, Yves,Curran, Dennis P.
, p. 2843 - 2846 (2007/10/03)
A four-step total synthesis of luotonin is deployed to make a small library of AB-ring substituted analogues. These analogues show weak activity in a standard topoisomerase I mediated DNA cleavage assay. Georg Thieme Verlag Stuttgart.
