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One-pot synthesis

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"One-pot" redirects here. For one-pot meals, seeStew.
One-pot preparation of 7-Hydroxyquinoline

Inchemistry aone-pot synthesis is a strategy to improve the efficiency of achemical reaction in which areactant is subjected to successive chemical reactions in just one reactor. This is much desired by chemists because avoiding a lengthyseparation process andpurification of the intermediatechemical compounds can save time and resources while increasingchemical yield.

An example of a one-pot synthesis is thetotal synthesis oftropinone or theGassman indole synthesis. Sequential one-pot syntheses can be used to generate even complex targets with multiplestereocentres, such asoseltamivir,[1] which may significantly shorten the number of steps required overall and have important commercial implications.

A sequential one-pot synthesis with reagents added to a reactor one at a time and withoutwork-up is also called atelescoping synthesis.

In one such procedure[2] the reaction of 3-N-tosylaminophenolI withacroleinII affords ahydroxyl substitutedquinolineIII through 4 sequential steps without workup of the intermediate products (see image). The addition of acrolein (blue) is aMichael reaction catalyzed byN,N-diisopropylamine, the presence ofethanol converts thealdehyde group to anacetal but this process is reversed whenhydrochloric acid is introduced (red). Theenolate reacts as anelectrophile in aFriedel-Crafts reaction with ring-closure. Thealcohol group iseliminated in presence ofpotassium hydroxide (green) and when in the final step the reaction medium is neutralized topH 7 (magenta) thetosyl group is eliminated as well.

References

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  1. ^Ishikawa, H.; Suzuki, T.; Hayashi, Y. (2009). "High-yielding synthesis of the anti-influenza neuramidase inhibitor (-)-oseltamivir by three "one-pot" operations".Angewandte Chemie International Edition in English.48 (7):1304–1307.doi:10.1002/anie.200804883.PMID 19123206.
  2. ^Cameron, M.; Hoerrner, R. S.; McNamara, J. M.; Figus, M.; Thomas, S. (2006). "One-Pot Preparation of 7-Hydroxyquinoline".Organic Process Research & Development.10 (1): 149.doi:10.1021/op0501545.
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