Premium
Ring opening reactions of 6‐oxo‐substituted spiro‐pyrrolidinediones: Synthesis of 4‐substituted‐1,5‐dihydro‐3‐hydroxy‐2‐oxo‐1,5‐diphenyl‐2 H ‐pyrroles
Author(s) -
Emerson David W.,
Titus Richard L.,
Jones Marlon D.
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350320
Subject(s) - chemistry , ring (chemistry) , cycloalkane , nonane , yield (engineering) , medicinal chemistry , organic chemistry , stereochemistry , catalysis , materials science , metallurgy
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 .