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Attempted Oxidative Deamination of N ‐Deacetylcolchicinoids with 3,5‐Di( tert ‐butyl)‐1,2‐benzoquinone: Synthesis of 2 H ‐1,4‐Benzoxazine‐Type Adducts
Author(s) -
Danieli Bruno,
Lesma Giordano,
Passarella Daniele,
Prosperi Davide,
Silvani Alessandra,
Bombardelli Ezio
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19990908)82:9<1502::aid-hlca1502>3.0.co;2-j
Subject(s) - chemistry , adduct , oxidative deamination , benzoquinone , deamination , oxidative phosphorylation , reagent , medicinal chemistry , 1,4 benzoquinone , quinone , stereochemistry , organic chemistry , biochemistry , enzyme
In an attempt to use 3,5‐di( tert ‐butyl)‐1,2‐benzoquinone for the oxidative deamination of N ‐deacetylcolchicine ( 4 ) and N ‐deacetylthiocolchicine (= N ‐deacetyl‐10‐demethoxy‐10‐(methylthio)colchicine; 5 ) to give the corresponding ketones 2 and 3 , the 2 H ‐1,4‐benzoxazine‐type adducts 8 / 9 and 11 / 12 , respectively, were formed instead, showing a new and unexpected behavior of Corey 's reagent. The adducts were separated and spectroscopically characterized, and a plausible scheme of formation is reported.