SYNTHESIS OF STEROIDAL D-RING FUSED PYRAZOLINES - STUDY OF REGIOCHEMISTRY OF ADDITION

被引:16
作者
GREEN, B
SHEU, KY
机构
[1] Department of Chemistry, University of Maine, Orano, ME
关键词
D-RING ADDITION; DIARYLPYRAZOLINES; DIPHENYLNITRILIMINES; REGIOCHEMISTRY;
D O I
10.1016/0039-128X(94)90061-2
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 [生物化学与分子生物学]; 081704 [应用化学];
摘要
The addition of diphenylnitrilimine and C-o-chlorodiphenylnitrilimine to 3 beta-hydroxyandrost-5,16-diene (3b) produced a 1/1 ratio of regioisomeric, 1,3-diaryl-2-pyrazolines (6a, 7a and 6b, 7b), whereas the addition of N-o-chlorodiphenylnitrilimine gave a 5/1 ratio in favor of the [17 alpha,16 alpha-d] regioisomer (7c). To further delineate the factors governing the regiochemistry of addition of diphenylnitrilimines to steroid 16-enes, additions were carried out on 16-acetyl-5 alpha-androst-16-ene (5b) and 1-acetylcyclopentene (10).
引用
收藏
页码:479 / 484
页数:6
相关论文
共 15 条
[1]
A NEW REACTION OF HYDRAZONES [J].
BARTON, DHR ;
OBRIEN, RE ;
STERNHELL, S .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (FEB) :470-&
[2]
BASTIDE J, 1973, B SOC CHIM FR II-CH, P2294
[3]
BIANCHI G, 1981, J CHEM RES-S, P6
[4]
FAJKOS J, 1961, COLLECT CZECH CHEM C, V26, P1118
[5]
GREEN B, 1975, Tetrahedron Letters, V33, P2807
[6]
SYNTHESIS OF STEROIDAL [16-ALPHA, 17-ALPHA-D]-2'-PYRAZOLINES AND [16,17-D]-PYRAZOLES [J].
GREEN, B ;
JENSEN, BL ;
LALAN, PL .
TETRAHEDRON, 1978, 34 (11) :1633-1639
[7]
FRONTIER MOLECULAR-ORBITALS OF 1,3 DIPOLES AND DIPOLAROPHILES [J].
HOUK, KN ;
SIMS, J ;
DUKE, RE ;
STROZIER, RW ;
GEORGE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) :7287-7301
[8]
ORIGIN OF REACTIVITY, REGIOSELECTIVITY, AND PERISELECTIVITY IN 1,3-DIPOLAR CYCLOADDITIONS [J].
HOUK, KN ;
SIMS, J ;
WATTS, CR ;
LUSKUS, LJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) :7301-7315
[9]
Huisgen R., 1963, ANGEW CHEM INT EDIT, V2, P633, DOI DOI 10.1002/ANIE.196306331
[10]
ALIPHATIC FRIEDEL-CRAFTS REACTIONS .2. THE ACYLATION OF CYCLOPENTENE [J].
JONES, N ;
TAYLOR, HT .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (DEC) :4017-4019