Aza-annulation as a versatile approach to the synthesis of non-benzodiazepene compounds for the treatment of sleep disorders

被引:24
作者
Benovsky, P
Stille, JR
机构
[1] ELI LILLY & CO,LILLY RES LABS,CHEM PROC RES & DEV,INDIANAPOLIS,IN 46285
[2] MICHIGAN STATE UNIV,DEPT CHEM,E LANSING,MI 48824
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(97)10297-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aza-annulation of enamino ester substrates has been demonstrated as an efficient alternative to the syntheses of non-benzodiazepine sleep inducers. Enamino ester substrates derived from aryl, thiophene, and indole functionality were prepared from the corresponding ethyl amines by isothiocyanate formation followed by acid catalyzed cyclization. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:8475 / 8478
页数:4
相关论文
共 31 条
  • [1] ASYMMETRIC FORMATION OF QUATERNARY CENTERS THROUGH AZA-ANNULATION OF CHIRAL BETA-ENAMINO ESTERS WITH ACRYLATE DERIVATIVES
    BARTA, NS
    BRODE, A
    STILLE, JR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (14) : 6201 - 6206
  • [2] Formation of dihydropyridone- and pyridone-based peptide analogs through aza-annulation of beta-enamino ester and amide substrates with alpha-amido acrylate derivatives
    Beholz, LG
    Benovsky, P
    Ward, DL
    Barta, NS
    Stille, JR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (04) : 1033 - 1042
  • [3] BHATTACHARJYA A, 1983, HETEROCYCLES, V20, P2397
  • [4] IMINE-ENAMINE ANNELATION - STEREOSELECTIVE SYNTHESES OF (+/-)-DEPLANCHEINE
    CALABI, L
    DANIELI, B
    LESMA, G
    PALMISANO, G
    [J]. TETRAHEDRON LETTERS, 1982, 23 (20) : 2139 - 2142
  • [5] AZA-ANNULATION AS A ROUTE TO HYDROXYLATED ALKALOID LIPIDS - THE SYNTHESIS OF (+/-)-PROSOPININE
    COOK, GR
    BEHOLZ, LG
    STILLE, JR
    [J]. TETRAHEDRON LETTERS, 1994, 35 (11) : 1669 - 1672
  • [6] CONSTRUCTION OF HYDROXYLATED ALKALOIDS (+/-)-MANNONOLACTAM, (+/-)-DEOXYMANNOJIRIMYCIN, AND (+/-)-PROSOPININE THROUGH AZA-ANNULATION
    COOK, GR
    BEHOLZ, LG
    STILLE, JR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) : 3575 - 3584
  • [7] DANIELI B, 1981, GAZZ CHIM ITAL, V111, P257
  • [8] EFFICIENT SYNTHESIS OF 1-ETHYL-2,3,4,6,7,12-HEXAHYDROINDOLO[2,3-A]QUINOLIZINE - KEY PRECURSOR TO EBURNANE ALKALOIDS
    DANIELI, B
    LESMA, G
    PALMISANO, G
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (03) : 109 - 109
  • [9] DANIELI B, 1984, SYNTHESIS-STUTTGART, P353
  • [10] TRICYCLIC PYRIDINE-DERIVATIVES WITH HIGH-AFFINITY TO THE CENTRAL BENZODIAZEPINE RECEPTOR
    FISCHER, U
    MOHLER, H
    SCHNEIDER, F
    WIDMER, U
    [J]. HELVETICA CHIMICA ACTA, 1990, 73 (04) : 763 - 781