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• W2952639098 abstract "Johnson-Claisen rearrangement of the Baylis-Hillman adducts has been reported by Basavaiah and co-workers to produce alkyl alk-4-enoate derivatives stereoselectively. Das and co-workers examined the Johnson-Claisen rearrangement of Baylis-Hillman adducts with triethyl orthoacetate and reported the applicability of I2/SiO2 or NaHSO4/SiO2 systems. We also examined the reaction of aza-BaylisHillman adducts and Baylis-Hillman adducts with N,Ndimethylformamide dimethylacetal (DMF-DMA), and we obtained cinnamyl amine derivatives in both cases. However, literature survey revealed that EschenmoserClaisen rearrangement of Baylis-Hillman adducts has not been reported. Thus, we decided to examine the Eschenmoser-Claisen rearrangement of Baylis-Hillman adducts (1a-c, 1g, and 1h) and cinnamyl alcohol derivatives (1d-f) with N,N-dimethylacetamide dimethylacetal (DMA-DMA) and report herein the results (Scheme 1 shows the synthesis of 2a and 2d as representative examples) Required starting materials 1a-h were synthesized according to the reported methods. The reaction conditions including the amounts of DMA-DMA, solvent, and temperature were examined and we found that optimum yields were obtained with 2.0 equiv of DMA-DMA in toluene at around 80-90 C. The results are summarized in Table 1 and the reaction mechanism is depicted in Scheme 1. For the secondary alcohol derivatives 1a-c, some ester compounds (3a: 5% in entry 1 and 3b: 4% in entry 2) were formed together (due to the competitive formation of intermediate III) and the yields of desired products 2a-c were moderate (69-71%). The products 2a and 2b were isolated as E/Z mixtures (ca. 9:1) as in the Johnson-Claisen rearrangement of the Baylis-Hillman adducts. The product 2c was obtained as a pure Z isomer, however, 2-dimethylaminomethyl-3phenylacrylonitrile (4, Z-form) was isolated together (13%). The primary alcohol derivatives 1d-f were cleanly converted into 2d-f in moderate to good yields (75-84%) and we could not find the corresponding ester derivatives in these cases. The Baylis-Hillman adducts of 2-cyclohexen-1-" @default.
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• W2952639098 date "2007-11-20" @default.
• W2952639098 modified "2023-10-17" @default.
• W2952639098 title "Eschenmoser-Claisen Rearrangement of Baylis-Hillman Adducts" @default.
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• W2952639098 doi "https://doi.org/10.5012/bkcs.2007.28.11.2093" @default.
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