Reaction of halomethyl ketones with thiols and selenols: substitution vs. reduction

R Seshadri, WJ Pegg, M Israel

Index: Seshadri, Ramakrishnan; Pegg, William J.; Israel, Mervyn Journal of Organic Chemistry, 1981 , vol. 46, # 12 p. 2596 - 2598

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Citation Number: 47

Abstract

ically promising adriamycin analogue>* for antitumor and structure-activity evaluation. Our initial synthetic approach involved reaction of 14-iodo-N-(trifluoroacetyl)-daunorubicin (1, X= I), a readily available intermediate in our laboratory, with alkane-and arenethiols, with the expectation of 2 (Scheme I), from which the corresponding free amino compounds could be achieved by alkaline hydrolysis of the trifluoroacetamide. However, treatment of 1 (X= I) ...