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Xanthobilirubic acid and its amides. Synthesis, spectroscopy, and solution structures
Author(s) -
Lightner D. A.,
Ma J.S.,
Adams T. C.,
Franklin R. W.,
Landen G. L.
Publication year - 1984
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.5570210128
Subject(s) - chemistry , lactam , propanoic acid , amide , pyrrole , intramolecular force , monomer , solvent , nuclear magnetic resonance spectroscopy , medicinal chemistry , stereochemistry , organic chemistry , polymer
Xanthobilirubic acid, 5‐[1,5‐didehydro‐3‐ethyl‐4‐methyl‐5‐oxo‐2 H ‐pyrrol‐2‐ylidene)methyl]‐2,4‐dimethyl‐1 H ‐pyrrol‐3‐propanoic acid, its methyl ester, amide, N ‐methylamide and dimethylamide, and kryptopyrromethenone have been synthesized and characterized spectroscopically. In d 6 ‐DMSO solution all pyrromethenones were monomeric, with lactam and pyrrole N‐Hs H‐bonded to solvent. In deuteriochloroform, the pyrromethenones preferred a dimeric form, with intramolecular H‐bonding between the lactam C = 0 of one unit and the lactam and pyrrole N‐Hs of the second.