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Synthesis 2017; 49(05): 1037-1042
DOI: 10.1055/s-0036-1588907
DOI: 10.1055/s-0036-1588907
paper
Blue Amino Acids Derived from Azulen-1-ylboronic Acid Pinacol Ester via the Petasis Reaction
Further Information
Publication History
Received: 06 September 2016
Accepted after revision: 04 October 2016
Publication Date:
22 November 2016 (online)
Abstract
Azulen-1-ylboronic acid pinacol ester undergoes a three-component Petasis reaction with amines and glyoxylic acid hydrate to give azulenylglycine derivatives in good yields. The progress of the reaction is indicated by a characteristic color change from violet to blue due to the altered π-conjugation of the azulene chromophore. The azulenylboronic ester is more reactive than its phenyl counterpart and even 2-styryl- and 2-thienylboronic pinacol esters, which have a strong electron-donating organyl group on boron. These results reflect the unique π-electron system of non-alternant azulene.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588907.
- Supporting Information
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