Water as the reaction medium for multicomponent reactions based on boronic acids

被引：84
作者：
Candeias, Nuno R. [1 ]
Cal, Pedro M. S. D. [1 ]
Andre, Vania [2 ]
Duarte, M. Teresa [2 ]
Veiros, Luis F. [2 ]
Gois, Pedro M. P. [1 ]
机构：
[1] Univ Lisbon, Fac Farm, iMed UL, P-1649003 Lisbon, Portugal
[2] Inst Super Tecn, Dept Engn Quim & Biol, Ctr Quim Estrutural, P-1049001 Lisbon, Portugal
来源：
TETRAHEDRON | 2010年 / 66卷 / 14期
关键词：
Boron; Multicomponent reactions; Petasis reaction; Boron heterocycles; MOLECULAR-ORBITAL METHODS; POLARIZABLE CONTINUUM MODEL; GAUSSIAN-TYPE BASIS; ORGANIC-REACTIONS; EQUILIBRIUM GEOMETRIES; BASIS-SETS; AMINES; ACCELERATION; 2H-CHROMENES;
D O I：
10.1016/j.tet.2010.01.084
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Water is a suitable medium for the Petasis-borono-Mannich multicomponent reaction Salicylaldehyde, glyoxalic acid, glycoaldehyde and glyoxal were reacted with several boronic acids and different amines affording alkylaminophenols, 2H-chromenes, alpha-amino acids, alpha-amino alcohols and 2-hydroxylmorpholines in good to high yields An efficient new one-pot method for the assembly of boron-heterocycles based on amino-acids, boronic acids and salicylaldehyde using water as the reaction media is presented The mechanisms of these reactions were studied by means of OFF calculations, and the effect of solvent on the calculated energy barriers was addressed, for different aldehydes (C) 2010 Elsevier Ltd All rights reserved
引用
收藏
页码：2736 / 2745
页数：10
相关论文
共 80 条
  • [1] Synthesis and characterization of boronates derived from non-symmetric amino-bis-phenols
    Abreu, A
    Alas, SJ
    Beltrán, HI
    Santillan, R
    Farfán, N
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (03) : 337 - 348
  • [2] A simple and effective approach to the synthesis of rhodanine derivatives via three-component reactions in water
    Alizadeh, Abdolati
    Rostamnia, Sadegh
    Zohreh, Nasrin
    Hosseinpour, Reza
    [J]. TETRAHEDRON LETTERS, 2009, 50 (14) : 1533 - 1535
  • [3] [Anonymous], J COMPUT CHEM
  • [4] Bisoxazaborolidines and boron complexes derived from tetradentate ligands:: synthesis and spectroscopic studies
    Barba, V
    Rodríguez, A
    Ochoa, ME
    Santillan, R
    Farfán, N
    [J]. INORGANICA CHIMICA ACTA, 2004, 357 (09) : 2593 - 2601
  • [5] X-ray analysis and structural characterization of 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononenones
    Beltrán, HI
    Zamudio-Rivera, LS
    Mancilla, T
    Santillan, R
    Farfán, N
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 657 (1-2) : 194 - 204
  • [6] Stereoselective synthesis of 2-hydroxymorpholines and aminodiols via a three-component boro-Mannich reaction
    Berrée, F
    Debache, A
    Marsac, Y
    Collet, B
    Girard-Le Bleiz, P
    Carboni, B
    [J]. TETRAHEDRON, 2006, 62 (17) : 4027 - 4037
  • [7] Boron-Based Diastereomerism and Enantiomerism in Imine Complexes Determination of the Absolute Configuration at Boron by CD Spectroscopy
    Braun, Manfred
    Schlecht, Sebastian
    Engelmann, Marco
    Frank, Walter
    Grimme, Stefan
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (31) : 5221 - 5225
  • [8] ON THE ORIGIN OF PRODUCT SELECTIVITY IN AQUEOUS DIELS-ALDER REACTIONS
    BRESLOW, R
    MAITRA, U
    [J]. TETRAHEDRON LETTERS, 1984, 25 (12) : 1239 - 1240
  • [9] SELECTIVE DIELS-ALDER REACTIONS IN AQUEOUS-SOLUTIONS AND SUSPENSIONS
    BRESLOW, R
    MAITRA, U
    RIDEOUT, D
    [J]. TETRAHEDRON LETTERS, 1983, 24 (18) : 1901 - 1904
  • [10] A new integral equation formalism for the polarizable continuum model: Theoretical background and applications to isotropic and anisotropic dielectrics
    Cances, E
    Mennucci, B
    Tomasi, J
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1997, 107 (08) : 3032 - 3041
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