Ring opening reactions of 6-oxo-substituted spiro-pyrrolidinediones: Synthesis of 4-substituted-1,5-dihydro-3-hydroxy-2-oxo-1,5-diphenyl-2H-pyrroles

✍ Scribed by David W. Emerson; Richard L. Titus; Marlon D. Jones

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1998
• Tongue: English
• Weight: 625 KB
• Volume: 35
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570350320

✦ Synopsis

Abstract

Reaction of 2‐oxocylalkaneglyoxylate esters with N‐phenylmethyleneaniline yields spiro compounds such as 2‐aza‐3,4,6,‐trioxo‐1,2‐diphenylspiro[4.4]nonane 4 and cycloalkane‐2‐aza‐3,4,6‐trioxo‐1,2‐diphenylspiro‐[4.5]decanes 5–7. These undergo solvolytic opening of the the oxocycloalkane ring to yield 4‐substituted‐1,5‐dihydro‐3‐hydroxy‐2‐oxo‐1,5‐diphenyl‐2__H__‐pyrroles 12–17.