The Crystal Structure of 3a,5,6a-Triphenyl-3,3a-dihydro-2H-furo[3,2-b]pyrrole-2,6(6aH)-dione

Under aqueous conditions dimethylamine, piperidine, and triethylamine catalyzed the ring-transformation reaction of triaryl-2H-furo[3,2-b]pyrrole-2,6(6aH)-diones (1), giving benzoylhydroxy-1-pyrrolines 2, which afforded benzoylpyrroles 3 upon acid-catalyzed dehydration. The lactone-ring-opened amides 6 were obtained in the reaction of 1 with methylamine, pyrrolidine, piperidine, and perhydroazepine at room temperature in ethanol. Pyrrolidine and piperidine produced pyrrolecarboxamides 7 when the reaction was carried out in aqueous ethanol under reflux. Amides 6 afforded 7 upon treatment with the amines under the above-mentioned conditions.

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Beckmann Reaction of Oximes of 3a-Aryl-5,6a-diphenyl-3a,6a-dihydro-2H-furo[3,2-b]pyrrole-2,6(3H)-dione and Its Derivatives

Mataka¹,

Suzuki²,

Sawada³

et al. 1993

Bulletin of the Chemical Society of Japan

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In the reaction with pyrrolidine, the (Z)-6-oxime (2) of 3a-aryl-5,6a-diphenyl-3a,6a-dihydro-2H-furo[3,2-b]pyrrole-2,6(3H)-dione (1) gave the (Z)-oxime (3) in which the lactone ring was opened. (Z)-Oxime 3 isomerized on silica gel to give (E)-oxime 4. Treatment of 2 with tosyl chloride in aqueous ethanolic sodium hydroxide afforded 5-aryl-2-cyano-2-phenyl-1H-pyrrol-3(2H)-ones (7) in yields of 41—90%, while both 3a and 4a gave the pyrroline-ring-opened product 8 in moderate yields.

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The Crystal Structure of 3a,5,6a-Triphenyl-3,3a-dihydro-2H-furo[3,2-b]pyrrole-2,6(6aH)-dione

Cited by 3 publications

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Photochemical substitution of halogenopyrrole derivatives

Photochemical substitution of halogenopyrrole derivatives

A Novel Ring Transformation of 3a,5,6a-Triaryl-3,3a-dihydro-2H-furo[3,2-b]pyrrole-2,6(6aH)-diones into 3-Aroyl-2,5-diarylpyrrole Derivatives

Beckmann Reaction of Oximes of 3a-Aryl-5,6a-diphenyl-3a,6a-dihydro-2H-furo[3,2-b]pyrrole-2,6(3H)-dione and Its Derivatives

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