[3+2] Dipolar Cycloaddition of 1-Pyrroline 1-Oxide with 2-Aryl-3-butenoates. Application to Prepare Bicyclic Heterocyclic Compounds
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概要
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Five- and six-membered ring systems containing a nitrogen atom at the bridgehead position were prepared via [3+2] dipolar cycloaddition of 1-pyrroline 1-oxide (5) with 2-aryl-3-butenoates. Cycloaddition of 5 with methyl 4,4-dichloro-2-[4-(tosyloxy) phenyl]-3-butenoate (4) gave 3 (and 2)-dichloromethyl-2 (and 3)-methoxycarbonyl-2 (and 3)-[4-(tosyloxy) phenyl]-2,3,3a, 4,5,6-hexahydropyrrolo [1,2-b] isoxazole (6 and 7) in a ratio of 52 : 10. Compound 6 was converted to 1-aza-3-r-hydroxy-4-c-methyl-3-t-[4-(tosyloxy) phenyl] bicyclo [3.3.0] octan-2-one (12) by treatment with zinc in aqueous acetic acid in one step or via the 4-chloromethyl analog of 12 (i.e., 11). On the other hand, cycloaddition of 5 with methyl 2-phenyl-3-butenoate (15) afforded methyl 2,3,3aα, 4,5,6-hexahydropyrrolo [1,2-b] isoxazol-2α-yl phenyl acetate (16) and 2-methoxycarbonyl-3-methyl-2-phenyl-2,3,3a, 4,5,6-hexahydropyrrolo [1,2-b] isoxazole (17) and its regioisomer (18) in a ratio fo 17 : 31 : 32. Treatment of 16 with zinc in aqueous acetic acid furnished 1-aza-4β-hydroxy-3α-phenyl-5aαH-bicyclo [4.3.0] nonan-2-one (20).
- 公益社団法人日本薬学会の論文
- 1985-01-25
著者
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樹林 千尋
東京薬科大学薬学部
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飯田 英夫
Tokyo College of Pharmacy
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樹林 千尋
Tokyo College of Pharmacy
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渡辺 四男也
Tokyo College of Pharmacy
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