Synthesis of steroidal diacyl hydrazines and their 1,3,4-oxadiazole derivatives.
Homogeneous catalytic hydrazinocarbonylation of some steroid derivatives possessing iodo-alkenyl moiety (17-iodo-androst-16-ene 1, 17-iodo-3-methoxy-estra-1,3,5(10),16-tetraene 2, 17-iodo-4-aza-4-methyl-androst-16-en-3-one 3 and 17-iodo-6beta-hydroxy-3alpha,5alpha-cycloandrost-16-ene 4) were carried out in the presence of a palladium catalyst, a base and acetic or benzoic hydrazide as the nucleophilic reagent. The corresponding N-acetamido-carbamoyl 1a-4a or N-benzamido-carbamoyl derivatives 1b-4b were obtained in high yields. Some of these derivatives served as starting materials for the synthesis of new steroidal 1,3,4-oxadiazole compounds.
Szarka
Zsolt
Z
Research Group for Petrochemistry of the Hungarian Academy of Sciences, Egyetem u. 8. (P.O. Box 158), H-8200 Veszprém, Hungary.
Skoda-Földes
Rita
R
Horváth
Judit
J
Tuba
Zoltán
Z
Kollár
László
L
D000107:Acetylation; D002384:Catalysis; D006834:Hydrazines / Q000138:chemical synthesis*; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis*; D010165:Palladium / Q000737:chemistry; D013256:Steroids / Q000138:chemical synthesis*
D006834:Hydrazines; D010069:Oxadiazoles; D013256:Steroids; C029424:hydrazine; D010165:Palladium