title: An Automated Process for a Sequential Heterocycle/Multicomponent Reaction: Multistep Continuous Flow Synthesis of 5-(Thiazol-2-yl)-3,4-Dihydropyrimidin-2(1H)-ones.
abstract: The first example of a sequential heterocycle formation/multicomponent reaction using an automated continuous flow microreactor assembly is reported. Consecutive Hantzsch thiazole synthesis, deketalization, and Biginelli multicomponent reaction provides rapid and efficient access to highly functionalized, pharmacologically significant 5-(thiazol-2-yl)-3,4-dihydropyrimidin-2(1H)-ones without isolation of intermediates. These complex small molecules are generated in reaction times less than 15 min and in high yields (39-46%) over three continuous chemical steps.
authors.affiliation: Apoptosis and Cell Death Research Program & Conrad Prebys Center for Chemical Genomics, Sanford-Burnham Medical Research Institute, 10901 N. Torrey Pines Rd., La Jolla, CA 92037, USA.
authors.forename: Nicholas
authors.initials: N
authors.lastname: Pagano
authors.affiliation: Apoptosis and Cell Death Research Program & Conrad Prebys Center for Chemical Genomics, Sanford-Burnham Medical Research Institute, 10901 N. Torrey Pines Rd., La Jolla, CA 92037, USA.
authors.forename: Ananda
authors.initials: A
authors.lastname: Herath
authors.affiliation: Apoptosis and Cell Death Research Program & Conrad Prebys Center for Chemical Genomics, Sanford-Burnham Medical Research Institute, 10901 N. Torrey Pines Rd., La Jolla, CA 92037, USA.
authors.forename: Nicholas D P
authors.initials: ND
authors.lastname: Cosford
keywords: Biginelli reaction; Hantzsch thiazole synthesis; flow chemistry; hydrobromic acid; microreactors; multistep synthesis