IODOTRIMETHYLSILANE-MEDIATED 2-MONOHALOGENATION OF 4-AZA-5-ALPHA-ANDROSTAN-3-ONE STEROIDS

被引：25

作者：

KING, AO

ANDERSON, RK

SHUMAN, RF

KARADY, S

ABRAMSON, NL

DOUGLAS, AW

机构：

[1] Department of Process Research, Merck Research Laboratories, Merck & Co., Inc., Rahway, New Jersey 07065

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 12期

关键词：

D O I：

10.1021/jo00064a028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective and high-yielding iodotrimethylsilane-mediated 2-monohalogenation of the title compounds is described, and a mechanism for the reaction is proposed. The method provides 2-iodo-4-aza-5alpha-androstan-3-one steroids in essentially quantitative yields.

引用

页码：3384 / 3386

页数：3

共 12 条

[1] SILYLATION-MEDIATED OXIDATION OF 4-AZA-3-KETOSTEROIDS WITH DDQ PROCEEDS VIA DDQ-SUBSTRATE ADDUCTS
BHATTACHARYA, A
DIMICHELE, LM
DOLLING, UH
DOUGLAS, AW
GRABOWSKI, EJJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (10) : 3318 - 3319
[2] EINE EINFACHE SYNTHESE VON L-LYSIN
BRENNER, M
RICKENBACHER, HR
[J]. HELVETICA CHIMICA ACTA, 1958, 41 (01) : 181 - 188
[3] THE PREPARATION AND AMMONOLYSIS OF ALPHA-HALOGEN DERIVATIVES OF EPSILON-CAPROLACTAM - A NEW SYNTHESIS OF LYSINE
FRANCIS, WC
THORNTON, JR
WERNER, JC
HOPKINS, TR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (23) : 6238 - 6244
[4] KING AO, 1991, Patent No. 5021575
[5] A FACILE ALPHA-IODINATION REACTION OF UNSATURATED AMIDES
KITAGAWA, O
HANANO, T
HIRATA, T
INOUE, T
TAGUCHI, T
[J]. TETRAHEDRON LETTERS, 1992, 33 (10) : 1299 - 1302
[6] FURTHER STUDIES OF BOND INSERTION AND NONSTEREOSPECIFIC BECKMANN REARRANGEMENTS IN 7-ALKYL-1-INDANONE OXIMES
LANSBURY, PT
MANCUSO, NR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (06) : 1205 - &
[7] NEW SYNTHESIS OF (+/-)-2-PIPERAZINECARBOXYLIC ACID
MEROUR, JY
COADOU, JY
[J]. TETRAHEDRON LETTERS, 1991, 32 (22) : 2469 - 2470
[8] CHEMISTRY OF ALPHA, ALPHA-DICHLOROSULFENYL CHLORIDES
PHILLIPS, WG
RATTS, KW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (10) : 1526 - &
[9] Rasmusson G. H., 1983, Patent, Patent No. [US4377584A, 4377584]
[10] AZASTEROIDS - STRUCTURE-ACTIVITY-RELATIONSHIPS FOR INHIBITION OF 5-ALPHA-REDUCTASE AND OF ANDROGEN RECEPTOR-BINDING
RASMUSSON, GH
REYNOLDS, GF
STEINBERG, NG
WALTON, E
PATEL, GF
LIANG, TM
CASCIERI, MA
CHEUNG, AH
BROOKS, JR
BERMAN, C
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) : 2298 - 2315

← 1 2 →