TY - JOUR
T1 - Thermodynamic Stability of Flavylium Salts as a Valuable Tool to Design the Synthesis of A-Type Proanthocyanidin Analogues
AU - Alejo-Armijo, Alfonso
AU - Parola, A. Jorge
AU - Pina, Fernando
AU - Altarejos, Joaquín
AU - Salido, Sofía
N1 - This study was supported by the University of Jaen (UJA081605) and by the Associate Laboratory for Green Chemistry-LAQV, which is financed by national funds from FCT/MCTES (UID/QUI/50006/2013) and cofinanced by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER-007265). A.A.-A. thanks the University of Jaen for a predoctoral fellowship and also the Fundacion Alfonso Martin Escudero for its current postdoctoral fellowship. Part of the work was supported by the Centro de Instrumentacion Cientifico-Tecnica of the University of Jaen.
PY - 2018/10/5
Y1 - 2018/10/5
N2 - A convenient method to synthesize A-type proanthocyanidin analogues from flavylium salts and Ï€-nucleophiles has been developed. It was found that the thermodynamic stability of the starting flavylium salt, assessed by the measurement of the apparent acidity constant (K′a), was the key parameter to design effective one-pot reactions between flavylium salts and nucleophiles such as phloroglucinol and (+)-catechin. When flavylium salts have a pK′a value of 1.7 or lower, the synthesis of the corresponding 2,8-dioxabyciclo[3.3.1]nonane derivative was properly achieved.
AB - A convenient method to synthesize A-type proanthocyanidin analogues from flavylium salts and Ï€-nucleophiles has been developed. It was found that the thermodynamic stability of the starting flavylium salt, assessed by the measurement of the apparent acidity constant (K′a), was the key parameter to design effective one-pot reactions between flavylium salts and nucleophiles such as phloroglucinol and (+)-catechin. When flavylium salts have a pK′a value of 1.7 or lower, the synthesis of the corresponding 2,8-dioxabyciclo[3.3.1]nonane derivative was properly achieved.
UR - http://www.scopus.com/inward/record.url?scp=85053687516&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.8b01780
DO - 10.1021/acs.joc.8b01780
M3 - Article
C2 - 30193456
AN - SCOPUS:85053687516
SN - 0022-3263
VL - 83
SP - 12297
EP - 12304
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 19
ER -