- Radical reactions with 3H-quinazolin-4-ones: Synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin
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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.
- Bowman, W. Russell,Elsegood, Mark R. J.,Stein, Tobias,Weaver, George W.
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p. 103 - 113
(2008/03/14)
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- Concise synthesis of quinazoline alkaloids, luotonins A and B, and rutaecarpine
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The total synthesis of luotonin A was achieved in excellent yield by using a Pd-assisted biaryl coupling reaction of N-(bromoquinolinyl)methylquinazolinone with Cy3P and KOAc. The successive treatment of luotonin A with NBS and aq. AgNO3 gave luotonin B in good yield. Although the Pd-assisted coupling reaction of N-(2-bromoindolyl)ethylquinazolinone with Cy3P and KOAc yielded rutaecarpine in poor yield, N-acetate under the same reaction conditions yielded the desired rutaecarpine directly in excellent yield. Graphical Abstract.
- Harayama, Takashi,Hori, Akihiro,Serban, Georgeta,Morikami, Yoshiaki,Matsumoto, Takuya,Abe, Hitoshi,Takeuchi, Yasuo
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p. 10645 - 10649
(2007/10/03)
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