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.
Attempted oxidative deamination of N-deacetylcolchicinoids with 3,5-di(tert-butyl)-1,2-benzoquinone: Synthesis of 2H-1,4-benzoxazine-type adducts / B. Danieli, G. Lesma, D. Passarella, D. Prosperi, A. Silvani, E. Bombardelli. - In: HELVETICA CHIMICA ACTA. - ISSN 0018-019X. - 82:9(1999), pp. 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
B. DanieliPrimo
;G. LesmaSecondo
;D. Passarella;A. SilvaniPenultimo
;
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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