I2-DMSO mediated multicomponent convergent synthesis of imidazo[2,1-a]isoquinoline derivatives via a triple in situ cross-trapping strategy

An I-2-DMSO mediated one-pot approach to imidazo[2,1-a]isoquinoline derivatives from readily available aryl methyl ketones and isoquinolin-1-amine has been demonstrated. This triple in situ cross-trapping strategy realizes the convergent integration of one self-sorting domino sequence with two linea...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 10; no. 16; pp. 4080 - 4085
Main Authors Tang, Yong-Xing, Zhuang, Shi-Yi, Liu, Jin-Yi, Zhou, You, Wang, Li-Sheng, Wu, Yan-Dong, Wu, An-Xin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 08.08.2023
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Convergence
Imidazole
Ketones
Organic chemistry
Oxidation
Physical Sciences
Science & Technology
Trapping
REGIOSELECTIVE SYNTHESIS
DOMINO REACTIONS
INTEGRATION
ANNULATION
METHYL KETONES
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Summary:An I-2-DMSO mediated one-pot approach to imidazo[2,1-a]isoquinoline derivatives from readily available aryl methyl ketones and isoquinolin-1-amine has been demonstrated. This triple in situ cross-trapping strategy realizes the convergent integration of one self-sorting domino sequence with two linear domino sequences, efficiently generating multiple C-C/C-N/C-S/C-I bonds, along with a new imidazole ring and one quaternary carbon center. Furthermore, the iodo group and methylthio group of the product can undergo further transformations through coupling or oxidation reactions, demonstrating the utility of this method in synthetic chemistry.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d3qo00724c