Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
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Outline of Final Research Achievements |
Selective synthesis of heterocycles by alkene cyclization of ethenetricarboxylates via conjugate addition has been studied. Reaction of E/Z-2-alkenyl esters and amides of ethenetricarboxylate with Lewis acids gave 2-oxotetrahydrofuran and pyrrolidine diastereomers stereospecifically. Sc(OTf)3-catalyzed cyclization of the allyl amides gave 2-oxopyrrolidine derivatives efficiently. Reaction of 2-hydrogen ethenetricarboxylate and E-cinnamylamines under the amide formation conditions led to pyrrolidine products in one pot, via intramolecular [2+2] and [4+2] cyclizations, depending on the substituents and the reaction conditions. Reaction with Z-cinnamylamines gave cis-fused tricyclic compounds via amide formation/[4+2] cyclization. The reactions with 3,3-diaryl-2-propenylamines gave cis- and trans-fused tricyclic compounds selectively, depending on the substituents, temperature and solvent. The cyclized products may be transformed to potentially useful compounds.
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