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 2H-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
Danieli, B., Lesma, G., Passarella, D., Prosperi, D., Silvani, A., Bombardelli, E. (1999). Attempted oxidative deamination of N-deacetylcolchicinoids with 3,5-di(tert-butyl)-1,2-benzoquinone: Synthesis of 2H-1,4-benzoxazine-type adducts. HELVETICA CHIMICA ACTA, 82(9), 1502-1508 [10.1002/(SICI)1522-2675(19990908)82:9<1502::AID-HLCA1502>3.0.CO;2-J].
Attempted oxidative deamination of N-deacetylcolchicinoids with 3,5-di(tert-butyl)-1,2-benzoquinone: Synthesis of 2H-1,4-benzoxazine-type adducts
PROSPERI, DAVIDE;
1999
Abstract
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 2H-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
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