SYNTHESIS AND UNUSUAL BECKMANN FRAGMENTATION REACTION OF SYN-3-METHOXY-6-ALPHA,17-BETA-DIHYDROXYESTRA-1,3,5(10)-TRIEN-7-ONE OXIME

被引：12
作者：
PEJANOVIC, VM [1 ]
PETROVIC, JA [1 ]
CSANADI, JJ [1 ]
STANKOVIC, SM [1 ]
MILJKOVIC, DA [1 ]
机构：
[1] UNIV NOVI SAD, FAC SCI, DEPT CHEM, YU-21000 NOVI SAD, YUGOSLAVIA
来源：
TETRAHEDRON | 1995年 / 51卷 / 48期
关键词：
D O I：
10.1016/0040-4020(95)00871-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Sodium borohydride reduction of anti-3-methoxy-17 beta-hydroxyestra-1,3,5(10)-trien-6,7-dione 7-oxime (4a) afforded syn-3-methoxy-6 alpha, 17 beta-dihydroxyestra-1,3,5(10)-trien-7-one oxime (5), which in thionyl chloride at -18 degrees C underwent Beckmann fragmentation reaction to the unexpected 3-methoxy-6-oxo-17 beta-hydroxy-6,7-secoestra-1,3,5(10)-trien-7-nitrile (6). A mechanism of this fragmentation process was proposed.
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收藏
页码：13379 / 13384
页数：6
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共 19 条
  • [1] Petrovic, Pejanovic, Miljkovic, Hranisavljevic, Steroids, 50, pp. 276-278, (1990)
  • [2] Bindray, Neyyarapally, Gupta, Kamboj, Anand, Antifertility agents. 8. Seco steroids. 2. 5,6-Secoestradiol and some related compounds, Journal of Medicinal Chemistry, 18, pp. 921-925, (1975)
  • [3] Jhingran, Gupta, Ray, Agarwal, Singht, Anand, Steroids, 42, pp. 627-634, (1983)
  • [4] Jhingran, Gupta, Ray, Agarwal, Singht, Anand, Indian J. Chem., 25 B, pp. 661-662, (1986)
  • [5] Durani, Agarwal, Saxena, Setty, Gupta, Kole, Ray, Anand, J. Steroid Biochem., 11, pp. 67-77, (1979)
  • [6] Eder, J. Steroid Biochem., 11, 1 A, pp. 55-60, (1979)
  • [7] Miljkovic, Petrovic, Beckmann fragmentation reaction of 3-methoxy-17.beta.-hydroxyestra-1,3,5(10)-trien-16-one oxime, The Journal of Organic Chemistry, 42, pp. 2101-2102, (1977)
  • [8] Miljkovic, Petrovic, Hadic, Tetrahedron, 34, pp. 3575-3577, (1978)
  • [9] Pejanovic, Petrovic, Djokovic, Miljkovic, Proceedings of Faculty of Sciences, Novi Sad, 21, pp. 31-36, (1991)
  • [10] Garza, Roa, Steroids, 42, pp. 469-474, (1983)
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