Volume 31, Issue 12
Heterocyclic Compounds
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ChemInform Abstract: 1,3,4,5-Tetrahydroazepin-2-ones by Dearomatizing Anionic Cyclization of N-Allyl-1-naphthamides.

Anjum Ahmed

Anjum Ahmed

Dep. Chem., Univ. Manchester, Manchester M13 9PL, UK

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Jonathan Clayden

Jonathan Clayden

Dep. Chem., Univ. Manchester, Manchester M13 9PL, UK

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Michael Rowley

Michael Rowley

Dep. Chem., Univ. Manchester, Manchester M13 9PL, UK

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First published: 09 June 2010

Abstract

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ChemInform Abstract

Treatment of 1-naphthamides (I) bearing N-allylic substituents with tBuLi and DMPU results in cyclization to seven-membered lactams providing the first example of an organolithium-CC cyclization leading to a seven-membered ring. No cyclization is observed in the case of substrate (IX).

chemical structure image

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