FeCl3-Promoted Annulation of 2-Haloindoles: Switchable Synthesis of Spirooxindole-chromeno[2,3-b]indoles and Spirooxindole-chromeno[3,2-b]indoles

Luo, Mupeng; Zhu, Xiwen; Liu, Rufeng; Yu, Shun‐Ming; Wei, Wanguo

doi:10.1021/acs.joc.9b03300

Cited by 14 publications

(3 citation statements)

References 68 publications

(23 reference statements)

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“…Moreover, their derivatives have been widely used as candidates for RNA-binding proteins and anticancer agents . At present, the reports on the synthesis of such fused heterocyclic scaffolds − are very few, which often suffered from limited substrates scope and harsh reaction conditions. Therefore, it is of great significance to develop new methods and catalysts for the synthesis under relatively mild conditions.…”

Section: Introductionmentioning

confidence: 99%

Design and Exploration of Iron Salt-Catalyzed Synthesis of Chromene[2,3-b] Indoles as a Laboratory Experiment for Undergraduates

et al. 2023

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Integrating new synthetic methods and experimental techniques from the latest research reports into undergraduate laboratory experiments is of great significance, as it enables students to learn the cutting-edge technology of organic chemistry and cultivates their experimental skills and innovative thinking. In this study, an experiment on the iron salt-catalyzed synthesis of chromone [2,3-b] indole derivatives, based on the latest report, was developed to train senior undergraduate students’ experimental skills and increase their basic knowledge in organic synthesis, especially those majoring in Organic Chemistry, Applied Chemistry, and Pharmaceutical Chemistry, among others. Incorporating this experiment into laboratory activities can strengthen students’ fundamental knowledge of organic chemistry, including Grignard reaction, substitution, addition, carbocation, tautomerism, intramolecular cyclization, and elimination, and enhance their skills in modern organic synthesis techniques, such as Schlenk technology for anhydrous and anaerobic operation, thin-layer chromatography for monitoring reaction progress, and column chromatography for the separation and purification of products. Additionally, this approach can help cultivate students’ scientific thinking and creativity and stimulate their enthusiasm for scientific research. The feasibility of introducing this latest scientific achievement into undergraduate laboratory experiments was verified by randomly selecting 12 undergraduates majoring in Applied Chemistry as pretest samples. The assessment results showed that the product yield obtained by different groups of students ranged from 72.6% to 85.8%, indicating a relatively high level of achievement, and the average score of the post-test was 81, which is a satisfactory outcome for such a comprehensive experiment.

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Section: Introductionmentioning

confidence: 99%

Design and Exploration of Iron Salt-Catalyzed Synthesis of Chromene[2,3-b] Indoles as a Laboratory Experiment for Undergraduates

et al. 2023

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“…Examples of such bioactive halogenated indoles include cytotoxic natural products represented by pibocin A, pibocin B, rivularin B, and rivularin D1 and therapeutic agents (such as dopamine receptor agonists bromocriptine and lergotrile) (Figure ). In addition, halogenated indoles have been frequently used for a plethora of metal-catalyzed cross-coupling reactions and as a versatile platform for the development of synthetic methodologies . The pervasive applications of halogenated indoles drive the development of many efficient synthetic methods .…”

Section: Introductionmentioning

confidence: 99%

Green Halogenation of Indoles with Oxone–Halide

Tang

Cheng

et al. 2023

J. Org. Chem.

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Oxidative functionalization of indoles is one of the most widely used approaches to exploit the synthetic utility of indoles. In continuation of our research interest in the green oxidation of indoles, we further explore the oxidation of indoles with oxone–halide and discover that the protecting group on the nitrogen of indoles plays a decisive role in controlling the pathways of indole oxidation with oxone–halide. An electron-withdrawing group on the nitrogen of indoles (N-EWG) enables C2 halogenation with stoichiometric halide, while C3 halogenation could be selectively achieved by using stoichiometric halide without dependence on the electronic property of the protecting group on the indole nitrogen. Different from our previous results obtained by using catalytic halide, these findings lead to the development of an environmentally friendly, efficient, and mild protocol for access to 2- or 3-haloindoles (chloro and bromo). As compared to the previous synthetic methods for 2-/3-haloindoles, our method exploits the in situ-generated reactive halogenating species from oxone–halide for halogenation of indoles and thus eliminates the use of stoichiometric halogenating agents and the production of toxic and hazardous organic byproducts derived from oxidants.

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“…The chromeno[2,3- b ]indole and spiroindoline skeletons are present in a large number of natural products and synthetic bioactive compounds (Figure ). While tremendous attention has been paid to their syntheses, , the development of creative divergent synthetic methodologies is still highly desirable.…”

mentioning

confidence: 99%

Divergent Synthesis of Chromenoindoles and Spiroindolines via Domino Reaction of Indolyl-Substituted Isocyanides with Quinone Esters

Wang

Dong

et al. 2022

Org. Lett.

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FeCl₃-Promoted Annulation of 2-Haloindoles: Switchable Synthesis of Spirooxindole-chromeno[2,3-b]indoles and Spirooxindole-chromeno[3,2-b]indoles

Cited by 14 publications

References 68 publications

Design and Exploration of Iron Salt-Catalyzed Synthesis of Chromene[2,3-b] Indoles as a Laboratory Experiment for Undergraduates

Design and Exploration of Iron Salt-Catalyzed Synthesis of Chromene[2,3-b] Indoles as a Laboratory Experiment for Undergraduates

Green Halogenation of Indoles with Oxone–Halide

Divergent Synthesis of Chromenoindoles and Spiroindolines via Domino Reaction of Indolyl-Substituted Isocyanides with Quinone Esters

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