An Automated Process for a Sequential Heterocycle/Multicomponent Reaction: Multistep Continuous Flow Synthesis of 5-(Thiazol-2-yl)-3,4-Dihydropyrimidin-2(1H)-ones

Nicholas Pagano; Ananda Herath; Nicholas D. P. Cosford

doi:10.1556/jfchem.2011.00001

Journal of Flow Chemistry

Volume/Issue:: Volume 1: Issue 1

An Automated Process for a Sequential Heterocycle/Multicomponent Reaction: Multistep Continuous Flow Synthesis of 5-(Thiazol-2-yl)-3,4-Dihydropyrimidin-2(1H)-ones

Authors:

Nicholas Pagano

Nicholas Pagano 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

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Ananda Herath

Ananda Herath 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

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, and

Nicholas D. P. Cosford

Nicholas D. P. Cosford 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

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Pages:: 28–31

Online Publication Date:: 29 Feb 2012

Publication Date:: 29 Feb 2012

Article Category:: Editorial

DOI:: https://doi.org/10.1556/jfchem.2011.00001

Keywords:: flow chemistry; microreactors; multistep synthesis; Hantzsch thiazole synthesis; hydrobromic acid; Biginelli reaction

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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.

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Journal of Flow Chemistry A Journal of the Flow Chemistry Society

Print ISSN:: 2062-249X

Online ISSN:: 2063-0212

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Journal of Flow Chemistry
Language	English
Size	A4
Year of Foundation	2011
Volumes per Year	1
Issues per Year	4
Founder	Áramlásos Kémiai Tudományos Társaság
Founder's Address	H-1031 Budapest, Hungary Záhony utca 7.
Publisher	Akadémiai Kiadó Springer Nature Switzerland AG
Publisher's Address	H-1117 Budapest, Hungary 1516 Budapest, PO Box 245. CH-6330 Cham, Switzerland Gewerbestrasse 11
Responsible Publisher	Chief Executive Officer, Akadémiai Kiadó
ISSN	2062-249X (Print)
ISSN	2063-0212 (Online)