Synthesis of three-dimensional fused and spirocyclic oxygen-containing cyclobutanone derivatives |
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| Affiliation: | 1. National Taras Shevchenko University of Kyiv, Volodymyrska Street, 64, Kyiv 01601, Ukraine;2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, Kyiv 02660, Ukraine;1. Department of Chemistry, Shivaji University, Kolhapur, 416004 Maharashtra, India;2. Sadguru Gadge Maharaj College, Karad, 415110 Maharashtra, India;1. Discovery Chemistry, Merck Research Laboratories, 2000 Galloping Hill Road, Kenilworth, NJ 07033, USA;2. Pharmaron Beijing Co., Ltd, 6 Tai-He Road, BDA, Beijing 100176, China;3. Discovery Biology, Merck Research Laboratories, 770 Sumneytown Pike, West Point, PA 19486, USA;1. Department of Pharmacy, School of Sciences, European University Cyprus, 6 Diogenis Str., Engomi, PO Box 22006, 1516 Nicosia, Cyprus;2. Department of Chemistry, University of Cyprus, PO Box 20537, 1678 Nicosia, Cyprus |
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| Abstract: | An approach to fused and spirocyclic oxygen-containing cyclobutanone derivatives based on ketene [2+2] cycloaddition with vinyl ethers is described. Using alicyclic chloroanhydrides as ketene sources as well as cyclic vinyl ethers in the reaction resulted in the formation of three-dimensional conformationally restricted building blocks of interest to medicinal chemistry and organic synthesis. In particular, 2-oxaspiro(bicyclo[3.2.0]heptane-7,1′-cycloalkane)-6-ones and 2-oxaspiro(bicyclo[4.2.0]octane-8,1′-cycloalkane)-6-ones were obtained. The procedure involves readily available and inexpensive starting materials and allows construction of complex molecular architectures on a large scale in a single run. |
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| Keywords: | Three-dimensional frameworks Cyclobutanes [2+2] cycloaddition Oxygen heterocycles Spiro compounds |
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