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.

show abstract

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

View full text Add to dashboard Cite

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.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

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

References 1 publication

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

Contact Info

Product

Resources

About