Synthesis of 16,17-seco-steroids with iminomethyl-2-pyridine and aminomethylene-2-pyridine structures as chiral ligands for copper ions and molecular oxygen activation

被引：12
作者：
Magyar, A
Schönecker, B
Wölfling, J
Schneider, G
Günther, W
Görls, H
机构：
[1] Univ Szeged, Dept Organ Chem, H-6720 Szeged, Hungary
[2] Univ Jena, Inst Organ Chem & Macromol Chem, D-07743 Jena, Germany
[3] Univ Jena, Inst Inorgan & Analyt Chem, D-07743 Jena, Germany
来源：
TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 18期
关键词：
D O I：
10.1016/S0957-4166(03)00539-1
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Starting from 16-oximino-3-methoxy-estra-1,3,5(10)-trien-17-one, the 16,17-seco-13alpha-carbaldehyde with a 16-nitrile function and its corresponding carboxylic acid have been synthesized via a Beckmann fragmentation. The corresponding 13alpha-amine is available by Curtius degradation of the carboxylic acid. Condensation of the carboxaldehyde with 2(aminomethyl)pyridine and the primary amine with pyridine-2-carboxaldehyde gave the corresponding iminomethyl-2-pyridine and the aminomethylene-2-pyridine compounds. Copper-mediated ligand hydroxylations with molecular oxygen were not successful. Reasons for this are discussed. (C) 2003 Elsevier Ltd. All rights reserved.
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页码：2705 / 2715
页数：11
相关论文
共 43 条
[1]   N,N-DIALKYLATED MONOPHENOLIC TRANS-2-PHENYLCYCLOPROPYLAMINES - NOVEL CENTRAL 5-HYDROXYTRYPTAMINE RECEPTOR AGONISTS [J].
ARVIDSSON, LE ;
JOHANSSON, AM ;
HACKSELL, U ;
NILSSON, JLG ;
SVENSSON, K ;
HJORTH, S ;
MAGNUSSON, T ;
CARLSSON, A ;
LINDBERG, P ;
ANDERSSON, B ;
SANCHEZ, D ;
WIKSTROM, H ;
SUNDELL, S .
JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (01) :92-99
[2]  
BACK TG, 1991, HETEROCYCLES, V32, P481
[3]  
Blain I, 2001, EUR J INORG CHEM, P205
[4]  
Blain I, 1998, EUR J INORG CHEM, P1297
[5]  
Blain I, 2000, EUR J INORG CHEM, P393
[6]   *UBERFUHRUNG VON OESTRON IN OESTRIOL [J].
BUTENANDT, A ;
SCHAFFLER, EL .
ZEITSCHRIFT FUR NATURFORSCHUNG, 1946, 1 (02) :82-87
[7]   GENERAL METHOD FOR REMOVAL OF A 4-METHYL GROUP FROM TRITERPENOIDS - SYNTHESIS OF 4-BETA-DEMETHYLGLYCYRRHETINIC ACID [J].
COHEN, KF ;
KAZLAUSKAS, R ;
PINHEY, JT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (19) :2076-2082
[8]  
*DAT COLL SOFTW, 1998, COLLECT DAT COLL SOF
[9]   MICROBIOLOGIC OXIDATION OF ESTRATRIENES AND ESTRATETRAENES BY STREPTOMYCES-ROSEOCHROMOGENES ATCC-13400 [J].
FERRER, JC ;
CALZADA, V ;
BONET, JJ .
STEROIDS, 1990, 55 (09) :390-394
[10]  
Frank É, 2002, SYNLETT, P1803
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