Syntheses and properties of benzodipyrrinones | Zendy

Boiadjiev Stefan E. | Zendy; Lightner David A. | Zendy

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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.

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