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Syntheses and properties of benzodipyrrinones
Author(s) -
Boiadjiev Stefan E.,
Lightner David A.
Publication year - 2003
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.5570400127
Subject(s) - chemistry , condensation , base (topology) , nuclear overhauser effect , proton nmr , stereochemistry , hydrogen , medicinal chemistry , nuclear magnetic resonance spectroscopy , organic chemistry , mathematical analysis , physics , mathematics , thermodynamics
2,3‐Benzannelated dipyrrinone analogs ( 1 and 2 ) of xanthobilirubic acid ( 3 ) are prepared by base‐catalyzed condensation of isoindolinone ( 5 ) and indolin‐2‐one ( 6 ) respectively, with methyl 3‐(2‐formyl‐3,5‐dimethyl‐1 H ‐pyrrol‐4‐yl)propanoate ( 4 ). Nuclear Overhauser effect H‐nmr studies indicate that both 1 and 2 adopt preferentially a syn‐Z configuration. The former forms a hydrogen‐bonded homodimer in nonpolar solvents; the latter is intramolecularly hydrogen bonded.