Synthesis of 5-phenyltetrazole and its N-methyl Derivatives in a Microreactor

Popova, E. A.; Абиев, Р. Ш.; Lappalainen, L. A.; Svetlov, S. D.; Andreeva, T. V.; Trifonov, R. E.; Островский, В. А.

doi:10.15255/cabeq.2013.1936

Cited by 12 publications

(4 citation statements)

References 7 publications

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“…Phenomena observed in experiments were systematically theoretically described in the papers of Kreutzer , , , by some other groups, e.g., that of Krishna , and of Schouten , and partly also by our team, e.g., Abiev , Abiev et al. , Popova et al , Svetlov and Abiev . Noncircular channels were in the focus of several papers, e.g., Thulasidas et al , , Triplett et al , Wörner et al , and Fletcher et al , .…”

Section: Gas‐liquid Flows In Capillaries: Theoretical Approach Simulmentioning

confidence: 74%

Hydrodynamics and Mass Transfer of Gas‐Liquid and Liquid‐Liquid Taylor Flow in Microchannels

2017

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Dedicated to Professor Rüdiger Lange on the occasion of his 65th birthday Hydrodynamics and mass transfer of both gas-liquid and liquid-liquid Taylor flow simulation in microchannels are reviewed. Theoretical approaches for description of hydrodynamic parameters and mass transfer characteristics are corroborated by comparison with available experimental results. Similarities and peculiarities of liquid-liquid flows versus gas-liquid Taylor flows in capillaries are discussed. Tools of mass transfer intensification of gas-liquid and liquid-liquid Taylor flow in microchannels are analyzed and optimal process conditions for gas-liquid Taylor flows are evaluated.

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Section: Gas‐liquid Flows In Capillaries: Theoretical Approach Simulmentioning

confidence: 74%

Hydrodynamics and Mass Transfer of Gas‐Liquid and Liquid‐Liquid Taylor Flow in Microchannels

2017

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“…[126] In another similar protocol, a cycloaddition between benzonitrile and dimethylammonium azide yielded 5-phenyltetrazole dimethylammonium salts. [127] Methyl azide in solution was generated in flow, and reacted with benzoyl cyanide at 200 °C. The resulting 1-methyl-5-benzoyltetrazole was obtained in 78 % yield (12 g scale), and it is a key precursor of picarbutrazox (IX), a new potent pesticide (Scheme 41).…”

Section: Nitrogen Containing Heterocycles: the Huisgen Reactionmentioning

confidence: 99%

“…In another similar protocol, a cycloaddition between benzonitrile and dimethylammonium azide yielded 5‐phenyltetrazole dimethylammonium salts . Methyl azide in solution was generated in flow, and reacted with benzoyl cyanide at 200 °C.…”

Section: ‐Membered Ringsmentioning

confidence: 99%

Flow Chemistry for Cycloaddition Reactions

2020

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Continuous flow reactors form part of a rapidly growing research area that has changed the way synthetic chemistry is performed not only in academia but also at the industrial level. This Review highlights the most recent advances in cycloaddition reactions performed in flow systems. Cycloadditions are atom-efficient transformations for the synthesis of carbo-and heterocycles, involved in the construction of challenging skeletons of complex molecules. The main advantages of translating these processes into flow include using intensified conditions, safer handling of hazardous reagents and gases, easy tuning of reaction conditions, and straightforward scaling up. These benefits are especially important in cycloadditions such as the copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), Diels-Alder reaction, ozonolysis and [2 + 2] photocycloadditions. Some of these transformations are key reactions in the industrial synthesis of pharmaceuticals.

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“…In addition, some azides are explosive which adds future complexity to their synthesis. Flow reactors have a considerable attraction for exothermic reactions because the high surface to volume ratio of the reactor enables excellent temperature control of the process …”

Section: Introductionmentioning

confidence: 99%