Multicapillary Flow Reactor: Synthesis of 1,2,5-Thiadiazepane 1,1-Dioxide Library Utilizing One-Pot Elimination and Inter-/Intramolecular Double aza-Michael Addition Via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)

Ullah, Farman; Zang, Qin; Javed, Salim; Zhou, Aihua; Knudtson, Christopher A.; Bi, Danse; Hanson, Paul R.; Organ, Michael G.

doi:10.1556/jfc-d-12-00015

Cited by 12 publications

(5 citation statements)

References 48 publications

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“…The Organ group has done extensive work developing and utilizing their microwave-assisted continuous-flow organic synthesis (MACOS) process in medicinal and combinatorial chemistry. − Their reactor is comprised of a stainless steel mixing chamber connected to glass capillaries which are positioned inside a microwave chamber. With their setup, a single capillary can be used to scale out a reaction to produce larger quantities of a single compound or in a recent report, four capillaries can be used for the simultaneous synthesis of four different compounds (Scheme ). Four stock solutions in isopropanol containing a sulfonamide 219 , DBU, and a different amine 220 for each capillary were reacted simultaneously.…”

Section: Temperaturementioning

confidence: 99%

The Hitchhiker’s Guide to Flow Chemistry

et al. 2017

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Flow chemistry involves the use of channels or tubing to conduct a reaction in a continuous stream rather than in a flask. Flow equipment provides chemists with unique control over reaction parameters enhancing reactivity or in some cases enabling new reactions. This relatively young technology has received a remarkable amount of attention in the past decade with many reports on what can be done in flow. Until recently, however, the question, "Should we do this in flow?" has merely been an afterthought. This review introduces readers to the basic principles and fundamentals of flow chemistry and critically discusses recent flow chemistry accounts.

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Section: Temperaturementioning

confidence: 99%

The Hitchhiker’s Guide to Flow Chemistry

et al. 2017

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“…We provide a short summary of this methodology to introduce the reader to several of these highyielding routes in one place. Similar synthetic paths were reported previously by us and the Hanson group [36][37][38][39][40][41][42][43][44][45]. In this work we combine all our synthetic methods for sevenand eight-membered ring -N,N-, -N,O-, and -N,S-sultams to give readers a more complete picture of the use of vinyl sulfonamides as starting materials to generate sultams.…”

Section: Introductionmentioning

confidence: 72%

A summary of seven- and eight-membered ring sultam syntheses via three Michael addition reactions

et al. 2015

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A series of seven- and eight-membered ring -N,O-, -N,N-, and -N,S-sultams were effectively synthesized via tandem reactions involving oxa-, aza-, and thia-Michael addition to vinyl sulfonamides. These reactions are summarized here since they enrich current synthetic methodologies for sultams and provide a good example of sultam diversity-oriented synthesis. All reactions proceeded under relatively mild and environmentally friendly conditions, and all these reactions are quite suitable for the rapid preparation of sultam compound libraries, which are valuable for biological activity explorations.

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“…MACOS was also implemented in seven‐membered heterocycle synthesis, described by Ullah et al ., in the preparation of a library of 1,2,5‐thiadiazepane‐1,1‐dioxide derivatives via a one‐pot elimination and inter‐/intramolecular double aza‐Michael addition strategy. The multicapillary flow reactor applied (100 °C/130 W) has proven to be effective for the generation of a wide scope of derivatives (50 examples ‐ 50–76 % yield) and scale‐up processes …”

Section: Heterocyclic Synthesismentioning

confidence: 99%

Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis

2019

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Flow Chemistry is a revolutionary field in Organic Chemistry. By changing the conventional methods and apparatus applied in the chemical synthesis, flow chemistry emerges as a game changer for organic synthesis laboratories, in both academia and industries. Considered as a sustainable practice, flow processes play an important role in the development of fine chemical products and in drug discovery development pro- [a] The main advantages of flow chemistry are that it allows the reaction to be carried out safely with high selectivity, high reproducibility and reduced energy consumption/carbon footprint. These features make this emerging technology for organic synthesis desirable for green and sustainable chemical synthesis, giving the chemist time for work planning and design, instead of using it in repetitive tasks, [5b,12] as expressed by the CHEM21 project by awarding a green flag for continuousflow reactions, in opposition to an amber flag for those performed under batch conditions. [13] Pedro Brandão received his MSc in Pharmaceutical Sciences from the Faculty of Pharmacy -University of Porto, in 2011. Pursuing his passion on studies in the field of Drug Discovery and Development, he is currently undergoing his PhD studies in Chemistry, in the field of Catalysis and Sustainability. His main focus of work is the discovery of new drug candidates through sustainable techniques. Marta Pineiro received her Ph.D. in Organic Chemistry in 2003 in the University of Coimbra, Portugal, and since 2002 has been enrolled at the University of Coimbra, being at present Auxiliary Professor. Her research interests are in the area of sustainable organic synthesis, microwave-assisted organic synthesis and synthesis and biological applications of tetrapyrrolic macrocycles. Teresa M. V. D. Pinho e Melo studied Chemistry at the University of Coimbra, where she graduated in 1985, got her M. 7191CPBA) as the oxidizing agent, avoiding the handling of this expensive and explosive reagent. [25] Recently, Morodo et al. explored the synthesis of two very important oxiranes (epichlorohydrin and glycidol) from biobased glycerol, under flow conditions. As depicted in Scheme 1, and using pimelic acid as the catalyst (10 mol-%), a sequential hydrochlorination/dichlorination process allows high conversion of glycerol (> 99 %) into 1,3-dichloro-2-propanol, followed by the quantitative conversion into a separable mixture of glycidol and epichlorohydrin (2:3). The separation of these two products is performed by an in-line membrane separation system, which allows the first product to be collected in the aqueous phase, while the second is collected in MTBE. This heterocycle can be further used as a synthetic precursor to relevant APIs bearing -amino alcohol moieties (e.g., propranolol, alprenolol and naftopidil). [26] Scheme 1. Sequential flow setup for the preparation of glycidol and epichlorohydrin, important APIs synthetic intermediates.Scheme 3. Synthesis and inline purification of a bicyclic aziridine (SGMR = silicon-glass microfluidic react...

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Multicapillary Flow Reactor: Synthesis of 1,2,5-Thiadiazepane 1,1-Dioxide Library Utilizing One-Pot Elimination and Inter-/Intramolecular Double aza-Michael Addition Via Microwave-Assisted, Continuous-Flow Organic Synthesis (MACOS)

Cited by 12 publications

References 48 publications

The Hitchhiker’s Guide to Flow Chemistry

The Hitchhiker’s Guide to Flow Chemistry

A summary of seven- and eight-membered ring sultam syntheses via three Michael addition reactions

Flow Chemistry: Towards A More Sustainable Heterocyclic Synthesis

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