Water as the reaction medium for multicomponent reactions based on boronic acids
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Details
| Original language | English |
|---|---|
| Pages (from-to) | 2736-2745 |
| Number of pages | 10 |
| Journal | Tetrahedron |
| Volume | 66 |
| Issue number | 14 |
| DOIs | |
| Publication status | Published - 3 Apr 2010 |
| Externally published | Yes |
| Publication type | A1 Journal article-refereed |
Abstract
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
Keywords
- Boron, Multicomponent reactions, Petasis reaction, Boron heterocycles, MOLECULAR-ORBITAL METHODS, DIELS-ALDER REACTIONS, POLARIZABLE CONTINUUM MODEL, GAUSSIAN-TYPE BASIS, ALPHA-AMINO-ACIDS, ORGANIC-REACTIONS, EQUILIBRIUM GEOMETRIES, TRANSITION-STATES, MANNICH REACTIONS, SOLVATION MODELS