Steroids

Novel and regiospecific synthesis of 2-amino estrogens via Zincke nitration

M Numazawa, K Kimura

Index: Numazawa, Mitsuteru; Kimura, Katsuhiko Steroids, 1983 , vol. 41, # 5 p. 675 - 682

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Citation Number: 17

Abstract

ABSTRACT An efficient synthesis of 2-aminoestrone (14), 2-aminoestradiol (15), 2-amino- 16u-hydroxyestrone (16) and 2-amigestriol (17) is described. 2, 4-Dibromo estrogens L-4 were regiospecifically converted to the corresponding 2-nitro-4-bromo derivatives 5-8 in quantitative yields, with Zincke nitration using sodium nitrite. Catalytic hydrogenation of the 2- nitro-4-bromides 5-3 over palladium-on-charcoal gave directly the desired 2-amino ...