Synthesis of functionalized diaryl sulfides by cyclocondensation of 3-arylthio-1-silyloxy-1,3-butadienes with 1,1,3,3-tetramethoxypropane, dimethyl allene-1,3-dicarboxylate, 1,1-bis(methylthio)-1-en-3-ones

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SCIENTIFIC WORK SYNTHESIS OF SOME 16,17-SECO- ANDROST-5-ENE DERIVATIVES

16,17-secoandrost-5-ene-16-nitrile (4) was synthesized by a three-stage procedure. First, the formyl group of compound 1 was reduced, to yield the alcohol 2. Compound 2 was further transformed to the mesyloxy derivative 3, whose reduction with NaBH 3CN gave compound 4. Apart from compound 4 as the main reaction product, two additional products were obtained, for which the GC/MS analysis suggested that they are Δ 8(14) and Δ 14 derivatives of compound 4. Compound 4 was transformed into 3β-hydroxy-16,17-secoandrost-5-ene-16-nitrile (7), the Oppenauer oxidation of which afforded 3-oxo-16,17-secoandrost-4-ene-16-nitrile (8). UDC 547.92.057:615.2 DOI: 10.2298/HEMIND100212009G There are various ways of reducing the C=O group of aldehydes and ketones to a CH2 [1]. The two oldest methods are the Wolff–Kishner reduction and the Clemensen reduction. In the Wolff–Kishner reduction, the aldehyde or ketone is heated with hydrazine hydrate an