Synthesis of some D-homo-D-aza estratriene derivatives | Zendy

Julijana Petrović | Zendy; Marija N. Sakač | Zendy; Katarina PenovGasi | Zendy; Vjera Pejanović | Zendy; Suzana Jovanović-Šanta | Zendy

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Synthesis of some D-homo-D-aza estratriene derivatives

Author(s) -

Julijana Petrović,

Marija N. Sakač,

Katarina PenovGasi,

Vjera Pejanović,

Suzana Jovanović-Šanta

Publication year - 2004

Publication title -

acta periodica technologica

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.134

H-Index - 15

eISSN - 2406-095X

pISSN - 1450-7188

DOI - 10.2298/apt0435225p

Subject(s) - nitrile , sodium borohydride , chemistry , derivative (finance) , medicinal chemistry , organic chemistry , catalysis , financial economics , economics

In this paper two synthetic routes for obtaining D-homo-D-aza estratriene derivatives were described. Namely, starting from 3-methoxyestra-1,3,5(10)-trien-16-oximino-17-one (1) 3-methoxy-17-aza-D-homoestra-1,3,5(10)-triene (5) was synthesized in two step. Another D-aza derivative was synthesize, starting from 3-methoxy-17-oxo-16,17-secoestra-1,3,5(10)-trien-16-nitrile (6). For that purpose, the seco-cyanoaldehyde was converted into its 17-ethylenacetal 7 followed by subsequent reduction of the nitrile function with sodium borohydride in the presence of cobalt chloride hexahydrate. Finally, under acidic conditions the obtained 16-amino-17-ethylenacetal 8 was transformed into 3-metoxy-17-aza-D-homoestra-1,3,5(10),17(17a)-tetraene (9)

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