Improved Synthesis of Monoprotected 5-and 6-Amino-2-azanorbornanes

被引：1
|
作者：
Dacenko, Oleksandr P. [2 ]
Manoylenko, Olga V. [2 ]
Grygorenko, Oleksandr O. [1 ,2 ]
Mykhailiuk, Pavel K. [1 ,2 ]
Volochnyuk, Dmitriy M. [2 ]
Shishkin, Oleg V. [3 ]
Tolmachev, Andrey A. [1 ,2 ]
机构：
[1] Kyiv Natl Taras Shevchenko Univ, Dept Chem, UA-01033 Kiev, Ukraine
[2] Enamine Ltd, Kiev, Ukraine
[3] Natl Acad Sci Ukraine, STC Inst Single Crystals, Kharkov, Ukraine
来源：
SYNTHETIC COMMUNICATIONS | 2011年 / 41卷 / 07期
关键词：
Bicyclic compounds; cycloadditions; diamines; molecular rigidity; peptidomimetics;
D O I：
10.1080/00397911003707196
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[image omitted] An improved synthesis of Boc-monoprotected 5- and 6-amino-2-azanorbornanes is reported. The synthetic scheme consists of five steps and allows multigram quantities of the title compounds to be obtained. The regio- and stereochemistries of the products are established by two-dimensional NMR experiments.
引用
收藏
页码：981 / 992
页数：12
相关论文
共 50 条
  • [1] Cyclic sulfates in the regioselective synthesis of 5-and 6-amino and 5-and 6-fluorohexofuranoses
    Fuentes, J
    Angulo, M
    Pradera, MA
    CARBOHYDRATE RESEARCH, 1999, 319 (1-4) : 192 - 198
  • [2] The synthesis of 5-and 6-benzyloxyindoles and attempts to prepare 5-and 6-hydroxyindoles therefrom
    Burton, H
    Stoves, JL
    JOURNAL OF THE CHEMICAL SOCIETY, 1937, : 1726 - 1728
  • [3] Electrochemical Synthesis of Unnatural Amino Acids Embedding 5-and 6-Membered Heteroaromatics
    Bombonato, Elena
    Fasano, Valerio
    Pecorari, Daniel
    Fornasari, Luca
    Castagnini, Francesco
    Marcaccio, Massimo
    Ronchi, Paolo
    ACS OMEGA, 2024, 9 (11): : 13081 - 13085
  • [4] Syntheses of 5-and 6-[2,3]-dihydrobenzofuran β-amino acids
    Coleman, PJ
    Hutchinson, JH
    Hunt, CA
    Lu, P
    Delaporte, E
    Rushmore, T
    TETRAHEDRON LETTERS, 2000, 41 (31) : 5803 - 5806
  • [5] The synthesis and separation of 5-and 6-aminofluoresceins
    Kopczacki, P
    PRZEMYSL CHEMICZNY, 2003, 82 (8-9): : 611 - 612
  • [6] Synthesis of 5-and 6-hydroxymethylfluorescein phosphoramidites
    Adamczyk, M
    Chan, CM
    Fino, JR
    Mattingly, PG
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (02): : 596 - 601
  • [7] Synthesis of 5-and 6-Carboxy-X-rhodamines
    Uddin, Md. Jashim
    Marnett, Lawrence J.
    ORGANIC LETTERS, 2008, 10 (21) : 4799 - 4801
  • [8] Synthesis of fluorine-18-labelled 5-and 6-fluoro-2-pyridinamine
    Abrahim, A
    Angelberger, P
    Kletter, K
    Müller, M
    Joukhadar, C
    Erker, T
    Langer, O
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2006, 49 (04): : 345 - 356
  • [9] Synthesis of substituted benzoindolinothiazepines using 5-and 6-nitroindolines
    Laconde, G
    Depreux, P
    Berthelot, P
    Hénichart, JP
    HETEROATOM CHEMISTRY, 2005, 16 (01) : 39 - 43
  • [10] Synthesis and reactivity of 5-and 6-hydroxy-benzo[b]furan-2-selenolates
    M. L. Petrov
    D. A. Androsov
    M. A. Abramov
    I. P. Abramova
    W. Dehaen
    Yu. I. Lyakhovetskii
    Russian Journal of Organic Chemistry, 2006, 42 : 1521 - 1527
12345