Regioselective reduction of 3-substituted 2,3-dihydrobenzothiadiazines with borohydrides

被引：4
作者：
Battisti, Umberto M. [1 ]
Cannazza, Giuseppe [1 ]
Carrozzo, Marina M. [1 ]
Braghiroli, Daniela [1 ]
Parenti, Carlo [1 ]
Rosato, Francesca [2 ]
Troisi, Luigino [2 ]
机构：
[1] Univ Modena & Reggio Emilia, Dipartimento Sci Farmaceut, I-4100 Modena, Italy
[2] Univ Salento, Dipartimento Sci & Tecnol Biol & Ambientali, I-73100 Lecce, Italy
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 33期
关键词：
2-Aminobenzenesulfonamide; 3-Chiral 2,3-dihydrobenzothiadiazines; Reduction; Sodium cyanoborohydride; ENANTIOMERIZATION; HYDROLYSIS; AFFINITY;
D O I：
10.1016/j.tetlet.2010.06.081
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient synthetic path for N-1 or N-2 alkyl-substituted 2-aminobenzenesulfonamides was developed based on regioselective reduction with NaBH(3)CN in different solvents (C) 2010 Elseviei Ltd All rights reserved
引用
收藏
页码：4433 / 4436
页数：4
相关论文
共 12 条
  • [1] BIRESSI MG, 1966, TETRAHEDRON LETT, V33, P3949
  • [2] Cannazza G, 2001, CHIRALITY, V13, P94, DOI 10.1002/1520-636X(2001)13:2<94::AID-CHIR1004>3.0.CO
  • [3] 2-O
  • [4] Cannazza G., 2010, CHIRALITY, DOI [DOI 10.1002/CHIR.20838, 10.1002/chir.20838]
  • [5] A novel class of allosteric modulators of AMPA/Kainate receptors
    Cannazza, Giuseppe
    Jozwiak, Krzysztof
    Parenti, Carlo
    Braghiroli, Daniela
    Carrozzo, Marina M.
    Puia, Giulia
    Losi, Gabriele
    Baraldi, Mario
    Lindner, Wolfgang
    Wainer, Irving W.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (04) : 1254 - 1257
  • [6] Enantiomerization and hydrolysis of (±)-7-chloro-3-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide by stopped-flow multidimensional high-performance liquid chromatography
    Cannazza, Giuseppe
    Carrozzo, Marina M.
    Braghiroli, Daniela
    Parenti, Carlo
    [J]. JOURNAL OF CHROMATOGRAPHY A, 2008, 1212 (1-2) : 41 - 47
  • [7] Simultaneous Determination of Enantiomerization and Hydrolysis Kinetic Parameters of Chiral N-Alkylbenzothiadiazine Derivatives
    Carrozzo, Marina M.
    Cannazza, Giuseppe
    Battisti, Umberto
    Braghiroli, Daniela
    Parenti, Carlo
    [J]. CHIRALITY, 2010, 22 (04) : 389 - 397
  • [8] New Fluorinated 1,2,4-Benzothiadiazine 1,1-Dioxides: Discovery of an Orally Active Cognitive Enhancer Acting through Potentiation of the 2-Amino-3-(3-hydroxy-5-methylisoxazol-4-yl) propionic Acid Receptors
    Francotte, Pierre
    Goffin, Eric
    Fraikin, Pierre
    Lestage, Pierre
    Van Heugen, Jean-Claude
    Gillotin, Florian
    Danober, Laurence
    Thomas, Jean-Yves
    Chiap, Patrice
    Caignard, Daniel-Henri
    Pirotte, Bernard
    de Tullio, Pascal
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (04) : 1700 - 1711
  • [9] Synthesis of Modified 4H-1,2,4-Benzothiadiazine-1,1-dioxides and Determination of their Affinity and Selectivity for Different Types of KATP Channels
    Lachenicht, Stefan
    Fischer, Andreas
    Schmidt, Claas
    Winkler, Marcus
    Rood, Achim
    Lemoine, Horst
    Braun, Manfred
    [J]. CHEMMEDCHEM, 2009, 4 (11) : 1850 - 1858
  • [10] 5′-alkyl-benzothiadiazides:: A new subgroup of AMPA receptor modulators with improved affinity
    Phillips, D
    Sonnenberg, J
    Arai, AC
    Vaswani, R
    Krutzik, PO
    Kleisli, T
    Kessler, M
    Granger, R
    Lynch, G
    Chamberlin, AR
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (05) : 1229 - 1248
12