Assembly of iodinated indolo[1,2-c]quinazoline amines via I2/CHP-promoted cascade annulation of isocyanides and diarylalkynes

Wu, Wanqing; Zhang, Min; Li, Meng; Jiang, Huanfeng; Nie, Biao

doi:10.1039/d3qo00799e

Org. Chem. Front.

2023

DOI: 10.1039/d3qo00799e

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Assembly of iodinated indolo[1,2-c]quinazoline amines via I₂/CHP-promoted cascade annulation of isocyanides and diarylalkynes

Wanqing Wu

Min Zhang

Meng Li

et al.

Abstract: Herein, a straightforward and efficient approach to iodinated indolo[1,2-c]quinazoline amines via I2/CHP-promoted cascade annulation of diarylalkynes and isocyanides has been described. This method features excellent regio- and chemoselectivities, good functional...

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2024

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Cited by 3 publications

References 42 publications

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Rh‐Catalyzed [4+3] Annulation of N‐Sulfonyl‐1,2,3‐Triazoles with 4‐Vinyl Indoles to Access Azepinoindoles

Wang,

Xu,

Feng

et al. 2024

Eur J Org Chem

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The present study provided an efficient synthesis pathway to the azepino[5,4,3‐cd]indoles using N‐sulfonyl‐1,2,3‐triazoles and 4‐vinylindoles through a cascade carbene insertion and intramolecular aza‐Michael addition. This method is distinguished by mild reaction conditions, straightforward operational steps, accessible starting materials, and broad substrate compatibility. Furthermore, the versatility of this reaction with various Michael acceptors significantly broadens the scope of potential substrates. The ability to further transform the resulting multifunctional products underscores the promising applications of this approach in indole nitrogen heterocyclic synthesis.

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Rh‐Catalyzed [4+3] Annulation of N‐Sulfonyl‐1,2,3‐Triazoles with 4‐Vinyl Indoles to Access Azepinoindoles

Wang,

Xu,

Feng

et al. 2024

Eur J Org Chem

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Palladium-Catalyzed Tandem Cyclization of Functional Diarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3-c]quinolines

Gao,

Wang,

Jiang

et al. 2024

J. Org. Chem.

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A novel strategy for the synthesis of various isochromeno [4,3-c]quinolines via palladium-catalyzed tandem cyclization of functional diarylalkynes with isocyanides has been developed. This approach features excellent chemo-and regioselectivities as well as good functional group tolerance. Notably, 6-phenylimino-6H-isochromeno[4,3-c]quinolin-11-amines and 11-amino-6Hisochromeno[4,3-c]quinolin-6-ones can be selectively constructed by employing different protecting groups of functional diarylalkynes. The gram-scale and late-stage modifications further demonstrate the synthetic value of this method.

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Palladium-catalyzed ligand-regulated divergent synthesis of pyrrole[2,3-b]indoles and ureas from 2-ethynylanilines and isocyanides

Zhang,

Zheng,

Jin

et al. 2024

Chem. Commun.

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Assembly of iodinated indolo[1,2-c]quinazoline amines via I₂/CHP-promoted cascade annulation of isocyanides and diarylalkynes

Abstract: Herein, a straightforward and efficient approach to iodinated indolo[1,2-c]quinazoline amines via I2/CHP-promoted cascade annulation of diarylalkynes and isocyanides has been described. This method features excellent regio- and chemoselectivities, good functional...

Cited by 3 publications

References 42 publications

Rh‐Catalyzed [4+3] Annulation of N‐Sulfonyl‐1,2,3‐Triazoles with 4‐Vinyl Indoles to Access Azepinoindoles

Rh‐Catalyzed [4+3] Annulation of N‐Sulfonyl‐1,2,3‐Triazoles with 4‐Vinyl Indoles to Access Azepinoindoles

Palladium-Catalyzed Tandem Cyclization of Functional Diarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3-c]quinolines

Palladium-catalyzed ligand-regulated divergent synthesis of pyrrole[2,3-b]indoles and ureas from 2-ethynylanilines and isocyanides

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