METHOD FOR INSERTION OF 1,2-DOUBLE BOND INTO 3-OXO-4-AZASTEROID COMPOUNDS Russian patent published in 2008 - IPC C07J73/00 

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention describes an improved method for synthesis of 17β-substituted 4-azaandrost-1-en-3-one of the general formula (I): wherein R means -OH, (C₁-C₄)-alkyl, (C₁-C₄)-alkenyl, phenyl, benzyl and others, or their pharmaceutically acceptable salts. Method involves insertion protective groups into 3-keto-4-aza (lactam) form of compound of the general formula (II): wherein R has indicated values to form compound of the general formula (III): wherein R₃ means trialkylsilyl, or in common with R₄ residue -C(O)-C(O)- or -C(O)-Y-C(O)- wherein R₄ means tert.-butyloxycarbonyl preferably; Y means -(CH₂)_n wherein n = 1-4, or ortho-phenylene. Then a synthesized compound is converted in the presence of a dehydrogenation catalyst of in the presence of benzoquinone, allylmethylcarbonate, allylethylcarbonate and/or allylpropylcarbonate, and ▵¹-double bond is introduced in 1,2-position followed by removal of protective groups and, if necessary, (when R means -OH) conversion to salts. Method provides the high yield and purity degree of synthesized compounds.

EFFECT: improved method of synthesis.

21 cl, 9 ex