Oxidant-controlled divergent transformations of 3-aminoindazoles for the synthesis of pyrimido[1,2-b]-indazoles and aromatic nitrile-derived dithioacetals
Literature Information
Publication Date
2019-08-09
DOI
10.1039/C9QO00847K
Impact Factor
5.281
Authors
Yao Zhou, Yixian Lou, Ya Wang
View Original
Abstract
The oxidant-controlled divergent reactivity of 3-aminoindazoles is presented herein. Diverse functionalized pyrimido[1,2-b]-indazole derivatives were obtained with good yields via a Lewis-acid promoted [3 + 3] annulation reaction between ketene dithioacetals and 3-aminoindazoles. When the reaction was performed using the Cu/[O] catalytic system, new reactivity for the ring-opening of 3-aminoindazoles via C–N bond activation was achieved, which enables the olefinic C–H arylation of ketene dithioacetals under mild conditions.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
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trans-2-{[(Tert-butoxy)carbonyl]amino}cyclobutane-1-carboxylic acid
CAS Number:
951173-25-4
Molecular Formula:
C10H17NO4
![3-[(3R,4R)-3-[(6-aminopyrimidin-4-yl)-methyl-amino]-4-methyl-1-piperidyl]-3-oxo-propanenitrile structure](https://static.chemtradehub.com/structs/164/1640971-60-3-83a4.webp "3-[(3R,4R)-3-[(6-aminopyrimidin-4-yl)-methyl-amino]-4-methyl-1-piperidyl]-3-oxo-propanenitrile structure")
3-[(3R,4R)-3-[(6-aminopyrimidin-4-yl)-methyl-amino]-4-methyl-1-piperidyl]-3-oxo-propanenitrile
CAS Number:
1640971-60-3
Molecular Formula:
C14H20N6O
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