Syntheses of Tetracyclic Indoline Derivatives Via Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade of 2‑Ethynyltryptamides

A gold­(I)-catalyzed hydroamination/cycloisomerization cascade reaction was developed to yield indolizino­[8,7-b]­indole and indolo­[2,3-a]-quinolizine derivatives from 2-ethynyltryptamides. The optimal conditions were determined by condition screening, and the functional group tolerances of these r...

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Published in:Journal of organic chemistry 2024-03, Vol.89 (5), p.3331-3344
Main Authors: Zhu, Jiang, Yang, Lu, Liu, Hairui, Sun, Shitao, Li, Jiaji, Zhang, Lianjie, Sun, Hanyang, Cheng, Maosheng, Lin, Bin, Liu, Yongxiang
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container_issue 5
container_start_page 3331
container_title Journal of organic chemistry
container_volume 89
creator Zhu, Jiang
Yang, Lu
Liu, Hairui
Sun, Shitao
Li, Jiaji
Zhang, Lianjie
Sun, Hanyang
Cheng, Maosheng
Lin, Bin
Liu, Yongxiang
description A gold­(I)-catalyzed hydroamination/cycloisomerization cascade reaction was developed to yield indolizino­[8,7-b]­indole and indolo­[2,3-a]-quinolizine derivatives from 2-ethynyltryptamides. The optimal conditions were determined by condition screening, and the functional group tolerances of these reactions were explored based on synthetic substrates. An insight into the explanation on the selectivity of the ring closure was obtained by density functional theory calculations. A plausible mechanism for the cascade reactions was proposed. Derivatization of the indolizino­[8,7-b]­indole and total synthesis of nauclefidine demonstrated the practicality of this strategy.
doi_str_mv 10.1021/acs.joc.3c02784
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title Syntheses of Tetracyclic Indoline Derivatives Via Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade of 2‑Ethynyltryptamides
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