Construction of novel steroidal isoxazolidinone derivatives under Vilsmeier-Haack conditions

被引:19
作者
Shamsuzzaman [1 ]
Khanam, Hena [1 ]
Mashrai, Ashraf [1 ]
Siddiqui, Nazish [2 ]
机构
[1] Aligarh Muslim Univ, Dept Chem, Aligarh 202002, Uttar Pradesh, India
[2] Aligarh Muslim Univ, Dept Illmul, Advia Ajmal Khan Tibbiya Coll, Aligarh 202002, Uttar Pradesh, India
关键词
6-Hydroxyiminocholestane; Isoxazolidinone; Vilsmeier reagent; Steroid; FUSED PYRIDINES; QUINOLINES; VERSATILE; 4-METHYLIDENEISOXAZOLIDIN-5-ONES; CONVERSION;
D O I
10.1016/j.tetlet.2012.11.105
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel expeditious and convenient synthesis of 5 alpha-cholestano-[5,6-c]-isoxazolidin-5'-ones based on the reaction of 5 alpha-6-hydroxyiminocholestanes with Vilsmeier-Haack reagent (DMF/POC1(3)) is described. The systems presented here, are novel scaffolds and have not been described before. Structural assignment of newly synthesized compounds was performed by IR, H-1 NMR, C-13 NMR, 2D H-1-H-1 COSY, MS and analytical data. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:874 / 877
页数:4
相关论文
共 38 条
[1]   NITRATION OF UNSATURATED STEROIDS [J].
ANAGNOSTOPOULOS, CE ;
FIESER, LF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (02) :532-536
[2]   DERIVED STEROIDS .1. CHOLESTERYL KETONES [J].
BAKER, RH ;
SQUIRE, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (04) :1487-1490
[3]   SYNTHESIS OF PHENOXYACETYL-N-SULFONYL CYCLOSERINE [J].
BALDWIN, JE ;
NG, SC ;
PRATT, AJ .
TETRAHEDRON LETTERS, 1987, 28 (37) :4319-4320
[4]   A GENERAL PROCEDURE FOR THE SYNTHESIS OF ISOXAZOLIDIN-5-ONES [J].
BALDWIN, JE ;
HARWOOD, LM ;
LOMBARD, MJ .
TETRAHEDRON, 1984, 40 (21) :4363-4370
[5]   SYNTHESIS AND PROPERTIES OF A SERIES OF STERICALLY HINDERED GUANIDINE BASES [J].
BARTON, DHR ;
ELLIOTT, JD ;
GERO, SD .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (09) :2085-2090
[6]   ENAMINE ANALOG REACTIONS OF ALDEHYDE-N,N-DIMETHHYDRAZONES [J].
BREHME, R ;
NIKOLAJEWSKI, HE .
TETRAHEDRON LETTERS, 1982, 23 (11) :1131-1134
[7]   Molecular rearrangements in the sterols III The constitution of i-cholesterol and of the isomeric ethers of cholesterol [J].
Ford, EG ;
Chakravorty, P ;
Wallis, ES .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1938, 60 :413-415
[8]   CHEMISTRY OF A NEW ANTIBIOTIC - LACTIVICIN [J].
HARADA, S ;
TSUBOTANI, S ;
HIDA, T ;
KOYAMA, K ;
KONDO, M ;
ONO, H .
TETRAHEDRON, 1988, 44 (21) :6589-6606
[9]   Hemiaminal generated by hydration of ketone-based nitrone as an N,O-centered nucleophile in organic synthesis [J].
Ishikawa, T ;
Nagai, K ;
Senzaki, M ;
Tatsukawa, A ;
Saito, S .
TETRAHEDRON, 1998, 54 (11) :2433-2448
[10]   THE SYNTHESIS AND X-RAY CRYSTAL-STRUCTURE OF A NOVEL VILSMEIER-HAACK ADDUCT - [TRIS(2-AMINOETHYL)AMINE][3-(DIMETHYLAMINO)-2-AMINOACRYLYL CHLORIDE]COBALT(III) CHLORIDE ZINC TETRACHLORIDE-WATER [J].
JACKSON, WG ;
SARGESON, AM ;
TUCKER, PA ;
WATSON, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) :533-540