Ru(II)-Catalysed Highly Regioselective C6 C-H/N-H Annulation of Indole-7-carboxamides with Alkynes for the Synthesis of Pyrrolo[3,2-h]isoquinolin-9-ones

IF 3.3 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2024-12-05 DOI:10.1002/asia.202401340

Pankaj Jadhav, Dr. Sudam Dawande

引用次数: 0

Abstract

We disclosed an efficient protocol for regioselective C6 C−H/N−H activation/annulation reaction of indole-7-carboxamides with alkynes to synthesize highly substituted pyrrolo[3,2-h]isoquinolin-9-one derivatives. Under optimized reaction conditions, electron-deficient and electron-rich internal alkynes reacted efficiently with various indole-7-carboxamides to deliver desired products in good to excellent yields. The synthetic utility of the product is demonstrated by its selective oxidation to the corresponding isatin derivative. Deuterium insertion and intermolecular competition experiments were also conducted to gain mechanistic insights.

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Ru(II)-催化吲哚-7-羧胺与炔的高区域选择性C6 C-H/N-H环合合成吡咯[3,2-h]异喹啉-9-酮

我们揭示了吲哚-7-羧基酰胺与炔的区域选择性C6 C-H/N-H活化/环化反应合成高取代吡咯[3,2-h]异喹啉-9- 1衍生物的高效方案。在优化后的反应条件下，贫电子和富电子内炔与各种吲哚-7-羧酰胺有效反应，以优异的收率得到所需的产物。通过选择性氧化生成相应的isatin衍生物，证明了该产物的合成用途。氘插入和分子间竞争实验也得到了机制的见解。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).