Aminohydroxylation and dihydroxylation of 4-aryl-1,2,5,6-tetrahydropyridines

被引:7
|
作者
Chang, Meng-Yang [1 ]
Lin, Chun-Yu
Wu, Tsun-Cheng
机构
[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan
[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan
关键词
cerium ammonium nitrate; oxidative addition; hydrogenation; 4-aryl-1,2,5,6-tetrahydropyridines; aminohydroxylation; dihydroxylation;
D O I
10.1016/j.tetlet.2006.05.174
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Substituted 3-amino-4-aryl-4-liydi-oxypiperidines and 4-aryl-3.4-dihvdroxypiperidiiies are synthesized in the modest overall yields starting from the regio- and stereoselective trans-aminohydroxylation and dihydroxylation of 4-aryl-1,15.6-tetrahydropyridines via CAN-mediated oxidative addition and hydrogenation. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5445 / 5449
页数:5
相关论文
共 50 条
  • [41] PHOSPHORUS NITROGEN-COMPOUNDS .31. N-PHOSPHINYLAMINO-1,2,5,6-TETRAHYDROPYRIDINES - ANALGESIC ACTIVITY AND EFFECT ON BLOOD-GLUCOSE
    CATES, LA
    LI, VS
    HEGDE, SS
    PHARMACEUTICAL RESEARCH, 1989, 6 (08) : 737 - 739
  • [42] MONOAMINE-OXIDASE CATALYSIS OF BIOCONVERSION OF PHYSIOLOGICALLY ACTIVE 1-METHYL-4-ARYL-1,2,3,6-TETRAHYDROPYRIDINES
    BACHURIN, SO
    SABLIN, SO
    GRISHINA, GV
    GAYDAROVA, EL
    DUBOVA, LG
    ZUBOV, ND
    BIOORGANICHESKAYA KHIMIYA, 1989, 15 (05): : 620 - 626
  • [43] Efficient access to chiral trans-2,6-dialkyl-1,2,5,6-tetrahydropyridines via allylation of chiral imines and ring-closing metathesis
    Felpin, FX
    Lebreton, J
    TETRAHEDRON LETTERS, 2003, 44 (03) : 527 - 530
  • [44] Synthesis and spatial structure of 3,5-dichloro-3,4,5,6-tetrahydropyridines
    Kastron, VV
    Mishnev, AF
    Skrastinsh, IA
    Duburs, GY
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1995, (08): : 1118 - 1123
  • [45] SYNTHETIC AND METABOLIC STUDIES OF 4-ACYLOXY-1,2,3,6-TETRAHYDROPYRIDINES
    DALVIE, DK
    ZHAO, Z
    CASTAGNOLI, N
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 204 : 183 - MEDI
  • [46] REGIOSELECTIVE SYNTHESIS OF TETRAHYDROPYRIDINES - 1-(4-METHOXYPHENYL)-1,2,5,6-TETRAHYDROPYRIDINE
    OVERMAN, LE
    FLANN, CJ
    MALONE, TC
    ORGANIC SYNTHESES, 1990, 68 : 188 - 197
  • [47] MOLECULAR-BASIS OF DISCREPANCIES IN NEUROTOXIC PROPERTIES AMONG 1-METHYL-4-ARYL-1,2,3,6-TETRAHYDROPYRIDINES
    BACHURIN, SO
    SABLIN, SO
    LERMONTOVA, NN
    SOLYAKOV, LS
    DUBOVA, LG
    TKACHENKO, SE
    MOLECULAR AND CHEMICAL NEUROPATHOLOGY, 1992, 17 (03) : 189 - 200
  • [48] Highly diastereoselective four-component synthesis of polysubstituted 1,4,5,6-tetrahydropyridines
    Anatoly N. Vereshchagin
    Taygib M. Iliyasov
    Kirill A. Karpenko
    Vladimir A. Smirnov
    Ivan E. Ushakov
    Michail N. Elinson
    Chemistry of Heterocyclic Compounds, 2021, 57 : 929 - 933
  • [49] Reactivity of 4-tert-butyldimethylsiloxy-1,2,3,6-tetrahydropyridines with hydrazines
    Figueroa, Javier
    Caballero, Esther
    Puebla, Pilar
    Tome, Fernando
    Medarde, Manuel
    MOLECULES, 2006, 11 (11) : 929 - 939
  • [50] SYNTHESIS AND PROPERTIES OF DECAHYDRO-1,8-NAPHTHYRIDINE AND 3,4,5,6-TETRAHYDROPYRIDINES
    ZONDLER, H
    PFLEIDER.W
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1972, 759 (MAY): : 84 - &