A Bifurcated Pathway to Thiazoles and Imidazoles Using a Modular Flow Microreactor

Baxendale, Ian R.; Ley, Steven V.; Smith, Christopher D.; Tamborini, Lucia; Voica, Ana-Florina

doi:10.1021/cc800070a

Cited by 48 publications

(16 citation statements)

References 60 publications

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“…It was discovered that when the dimethyll -tartrate and trimethyl orthoformate were premixed, rapid formation of an intermediate diacetal occurred, which was observed using the ReactIR flow cell ( Scheme 17 ). This proved to be an important observation and optimization of Guanadine library [80] Thiazole library [79] Oxazole library [83] Grossamide [81] Zolpidem [72] Meclinertant SR 48692 [74] Casein Kinase Inhibitors library [77] Aminopyrrolidines [78] Polypeptides [82] Scheme 15 A range of other targeted structures achieved using multi-step flow synthesis.…”

Section: Reaction Monitoring With In-line Diagnosticsmentioning

confidence: 99%

Flow chemistry approaches directed at improving chemical synthesis

Baxendale

Brocken

Mallia

2013

Green Processing and Synthesis

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Flow synthesis offers many advantages when applied to the processing of difficult or dangerous chemical transformations. Furthermore, continuous production allows for rapid scale up of reactions without significant redevelopment of the routes. Importantly, it can also provide a versatile platform from which to build integrated multi-step transformations, delivering more advanced chemical architectures. The construction of multi-purpose micro and meso flow systems, that utilize in-line purification and diagnostic capabilities, creates a scenario of seamless connectivity between sequential steps of a longer chemical sequence. In this mini perspective, we will discuss our experience of target orientated multi-step synthesis as presented at the recent inaugural meeting of LEGOMEDIC at Namar University, Belgium.

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Section: Reaction Monitoring With In-line Diagnosticsmentioning

confidence: 99%

Flow chemistry approaches directed at improving chemical synthesis

Baxendale

Brocken

Mallia

2013

Green Processing and Synthesis

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“…The microfluidic setup for the flow synthesis of 1-(thiazol-2-yl)propan-2-one derivatives ( 2 ) is outlined in Table 1. Our procedure is inspired by the reported microreactor syntheses of 2-aminothiazoles [17] and 4,5-disubstituted thiazoles [18]. …”

Section: Resultsmentioning

confidence: 99%

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

Pagano¹,

Herath

Cosford

2011

J Flow Chem

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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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“…Reacting various isothiocyanates and ethyl isocyanoacetate provided a bifurcated route to the preparation of thiazoles and imidazoles in a modular flow reactor [32]. Yields in the range of 50% of the desired thiazole were obtained.…”

Section: Five-membered Ring Heterocycles With Two Heteroatomsmentioning

confidence: 99%