Issue 19, 2019

Oxidant-controlled divergent transformations of 3-aminoindazoles for the synthesis of pyrimido[1,2-b]-indazoles and aromatic nitrile-derived dithioacetals

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.

Graphical abstract: Oxidant-controlled divergent transformations of 3-aminoindazoles for the synthesis of pyrimido[1,2-b]-indazoles and aromatic nitrile-derived dithioacetals

Supplementary files

Article information

Article type
Research Article
Submitted
03 Jul 2019
Accepted
09 Aug 2019
First published
09 Aug 2019

Org. Chem. Front., 2019,6, 3355-3359

Oxidant-controlled divergent transformations of 3-aminoindazoles for the synthesis of pyrimido[1,2-b]-indazoles and aromatic nitrile-derived dithioacetals

Y. Zhou, Y. Lou, Y. Wang and Q. Song, Org. Chem. Front., 2019, 6, 3355 DOI: 10.1039/C9QO00847K

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