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Oxazolo analogs of the actinomycin D chromophore
Author(s) -
Sengupta Sisir K.,
Tinter S. Karin,
Modest Edward J.
Publication year - 1978
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.5570150128
Subject(s) - chemistry , acetaldehyde , benzaldehyde , pyruvic acid , chromophore , ring (chemistry) , tricyclic , condensation reaction , stereochemistry , aldehyde , condensation , medicinal chemistry , benzoquinone , organic chemistry , physics , ethanol , thermodynamics , catalysis
Condensation of a tricyclic phenoxazin‐2‐amino‐3‐one (a model for the actinomycin D ring system) with acetaldehyde or benzaldehyde or with pyruvic acid as an acetaldehyde precursor gave tetracyclic 5 H ‐oxazolo[4,5‐ b ]phenoxazines. The pyruvic acid reaction proceeds efficiently in one step. The latter compounds were oxidized in a novel reaction by 2,3‐dichloro‐5,6‐dicyano‐benzoquinone exclusively at position 8 in the benzenoid ring. Uv, ir, nmr, and mass spectrometric data are reported.