TY - JOUR
T1 - A diversity oriented synthesis of 10H-pyridazino[6,1-b]quinazolin-10-ones and their ring opening derivatives
AU - Schuler, Elisabeth
AU - Teixidó, Jordi
AU - Michelotti, Enrique L.
AU - Borrell, José I.
PY - 2005/9
Y1 - 2005/9
N2 - A parallel method for the synthesis of the title compounds is described. Thus, anthranilic acids (2) were treated with 3-chloropyridazines (3) in a 2:1 propanol:water mixture using HCI as acid catalyst to yield 10H-pyridazino[6,1-b] quinazolin-10-ones (1). Compounds (1) present three diversity centers (R 1, R2 and R3). The range of chemically acceptable substituents at each center has been evaluated. The ring opening of compounds 1 afforded benzoic acids 5 which in turn are easily ciclyzed to 1H-pyridazino[6,1-D]quinazoline-2,10-diones (4) with TFA. The N- and O-alkylation of 4{1,1} has been also studied.
AB - A parallel method for the synthesis of the title compounds is described. Thus, anthranilic acids (2) were treated with 3-chloropyridazines (3) in a 2:1 propanol:water mixture using HCI as acid catalyst to yield 10H-pyridazino[6,1-b] quinazolin-10-ones (1). Compounds (1) present three diversity centers (R 1, R2 and R3). The range of chemically acceptable substituents at each center has been evaluated. The ring opening of compounds 1 afforded benzoic acids 5 which in turn are easily ciclyzed to 1H-pyridazino[6,1-D]quinazoline-2,10-diones (4) with TFA. The N- and O-alkylation of 4{1,1} has been also studied.
KW - Agrochemistry
KW - Diversity
KW - Parallelization
KW - Pyridazino[6,1-b]quinazolines
UR - https://www.scopus.com/pages/publications/33745019126
UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=pure_univeritat_ramon_llull&SrcAuth=WosAPI&KeyUT=WOS:000237566100008&DestLinkType=FullRecord&DestApp=WOS
M3 - Article
AN - SCOPUS:33745019126
SN - 0001-9704
VL - 62
SP - 401
EP - 409
JO - Afinidad
JF - Afinidad
IS - 519
ER -