Cu()-Mediated aerobic oxidative synthesis of sulfonated chromeno[4,3-]pyrazol-4(2)-ones

Herein, starting with propiolates and sulfonyl hydrazides, we developed a concise and facile synthesis of 2-sulfonylated chromeno [4,3- c ]pyrazol-4(2 H )-ones or 2,5-dihydro-4 H -pyrazolo[4,3- c ]quinolin-4-ones via Cu( ii )-promoted oxidative cascade C-C/C-N bond formation. This protocol has the a...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-07, Vol.2 (28), p.5575-5581
Main Authors: Zhou, Quan, Yu, Hai-Yan, Zhou, Yaqing, Wei, Jing-Ru, Wang, Lei
Format: Article
Language:English
Subjects:
Alkynes
Alkynes - chemistry
Atom economy
Copper
Functional groups
Hydrazides
Oxidation-Reduction
Oxidative Stress
Synthesis
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Summary:Herein, starting with propiolates and sulfonyl hydrazides, we developed a concise and facile synthesis of 2-sulfonylated chromeno [4,3- c ]pyrazol-4(2 H )-ones or 2,5-dihydro-4 H -pyrazolo[4,3- c ]quinolin-4-ones via Cu( ii )-promoted oxidative cascade C-C/C-N bond formation. This protocol has the advantages of atom economy and good functional group tolerance. The primary mechanism studies indicate that the reaction involves a free-radical process as well as terminal alkyne C-H activation. A concise and facile synthesis of 2-sulfonylated chromeno [4,3- c ]pyrazol-4(2 H )-ones and 2,5-dihydro-4 H -pyrazolo[4,3- c ]quinolin-4-ones via Cu( ii )-promoted oxidative cascade C-C/C-N bond formation is described.
ISSN:1477-0520
1477-0539
DOI:10.1039/d2ob00639a