Palladium-Catalyzed\nTandem Cyclization of Functional\nDiarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3‑<i>c</i>]quinolines

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

Publication Details

Journal
Figshare
Published
2024-12-10
DOI
https://doi.org/10.1021/acs.joc.4c02142.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Palladium-Catalyzed\nTandem Cyclization of Functional\nDiarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3‑c]quinolines

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Catalytic C–H Functionalization Methods
article

Palladium-Catalyzed\nTandem Cyclization of Functional\nDiarylalkynes and Isocyanides for the Assembly of Isochromeno[4,3‑c]quinolines

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Abstract

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

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Catalytic C–H Functionalization Methods
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