Reactions of 4-azacholest-5-en-3-one, 6-azacholest-4-en-7-one, and their N-methyl derivatives with electrophilic reagents

被引：7
作者：
Morzycki, JW
Wilczewska, AZ
机构：
[1] Institute of Chemistry, University of Warsaw, Bialystok Branch, 15-443 Bialystok
来源：
TETRAHEDRON | 1996年 / 52卷 / 44期
关键词：
D O I：
10.1016/0040-4020(96)00847-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reactions of four steroidal ene-lactams with electrophilic reagents, such as bromine, acetyl nitrate or CrO3, were studied. The initial electrophilic attack took place on the terminal carbon atom of the enamide system. In some cases further reactions at the allylic position were observed There were no reactions at the nitrogen atom or in the a position to the lactam carbonyl group. Copyright (C) 1996 Elsevier Science Ltd.
引用
收藏
页码：14057 / 14068
页数：12
相关论文
共 17 条
  • [1] DELETION OF STEROID 5-ALPHA-REDUCTASE 2-GENE IN MALE PSEUDOHERMAPHRODITISM
    ANDERSSON, S
    BERMAN, DM
    JENKINS, EP
    RUSSELL, DW
    [J]. NATURE, 1991, 354 (6349) : 159 - 161
  • [2] THE SYNTHESIS OF SOME NOVEL N-CHLORO-DELTA(1)-4-AZASTEROIDS BY EFFICIENT N-CHLORINATION OF AZASTEROID LACTAMS WITH TRICHLOROISOCYANURIC ACID
    BACK, TG
    CHAU, JHL
    DYCK, BP
    GLADSTONE, PL
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1991, 69 (09): : 1482 - 1486
  • [3] BACK TG, 1979, TETRAHEDRON LETT, P4931
  • [4] SYNTHESIS AND ANTIMICROBIAL PROPERTIES OF 17BETA-ISOPENTYLOXY-4-AZA-5ALPHA-ANDROSTANE AND 4-METHYL DERIVATIVE
    DOORENBOS, NJ
    SOLOMONS, WE
    [J]. JOURNAL OF PHARMACEUTICAL SCIENCES, 1973, 62 (04) : 638 - 640
  • [5] 6-AZASTEROIDS - STRUCTURE-ACTIVITY-RELATIONSHIPS FOR INHIBITION OF TYPE-1 AND TYPE-2 HUMAN 5-ALPHA-REDUCTASE AND HUMAN ADRENAL 3-BETA-HYDROXY-DELTA(5)-STEROID DEHYDROGENASE 3-KETO-DELTA(5)-STEROID ISOMERASE
    FRYE, SV
    HAFFNER, CD
    MALONEY, PR
    MOOK, RA
    DORSEY, GF
    HINER, RN
    CRIBBS, CM
    WHEELER, TN
    RAY, JA
    ANDREWS, RC
    BATCHELOR, KW
    BRAMSON, HN
    STUART, JD
    SCHWEIKER, SL
    VANARNOLD, J
    CROOM, S
    BICKETT, DM
    MOSS, ML
    TIAN, GC
    UNWALLA, RJ
    LEE, FW
    TIPPIN, TK
    JAMES, MK
    GRIZZLE, MK
    LONG, JE
    SCHUSTER, SV
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (15) : 2352 - 2360
  • [6] BENIGN PROSTATIC HYPERPLASIA - PATHOGENESIS AND MEDICAL THERAPY
    GELLER, J
    [J]. JOURNAL OF THE AMERICAN GERIATRICS SOCIETY, 1991, 39 (12) : 1208 - 1216
  • [7] SYNTHESIS OF 6-AZACHOLESTEN-3-ONES - POTENT INHIBITORS OF 5-ALPHA-REDUCTASE
    HAFFNER, C
    [J]. TETRAHEDRON LETTERS, 1995, 36 (23) : 4039 - 4042
  • [8] THE INTRODUCTION OF OXYGEN AND NITROGEN INTO THE B-RING OF THE STEROID NUCLEUS
    JACOBS, TL
    BROWNFIELD, RB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (15) : 4033 - 4039
  • [9] NOVEL CONVERGENT SYNTHESIS OF SIDE-CHAIN-MODIFIED ANALOGS OF 1-ALPHA,25-DIHYDROXYCHOLECALCIFEROL AND 1-ALPHA,25-DIHYDROXYERGOCALCIFEROL
    KUTNER, A
    PERLMAN, KL
    LAGO, A
    SICINSKI, RR
    SCHNOES, HK
    DELUCA, HF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) : 3450 - 3457
  • [10] MAPPUS E, 1979, J CHEM RES S, V42
12