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Synfacts 2006(9): 0885-0885  
DOI: 10.1055/s-2006-942061
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Lateral Metallation-Cycloannulation Synthesis of 2H-quinolizin-2-ones

Contributor(s): Victor Snieckus, Todd Macklin
S. R. Natarajan*, M.-H. Chen*, S. T. Heller, R. M. Tynebor, E. M. Crawford, C. Minxiang, H. Kaizheng, J. Dong, B. Hu, W. Hao, S.-H. Chen
Merck Research Laboratories, Rahway, USA and WuXi Pharmatech, Shanghai, P. R. of China
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

A new synthetic route to substituted 2H-quinolizin-2-ones via acylation and intra­molecular annulation is reported. Lateral lithiation, even in the presence of a secondary amide substituent, followed by acylation with methyl alkynoate leads to a product which, upon heating in aceto­nitrile, furnishes the 2H-quinolizin-2-ones in low to modest yields. Several aza-quinolizin-2-ones, shown in the scheme, have also been prepared in modest overall yields.