Tandem Cyclization−Annulation of α‐Acidic Isocyanides with 2‐Methyleneaminochalcones: Synthesis of Pyrrolo[2,3‐<i>c</i>]quinoline Derivatives

Dong, Jinhuan; Wang, Xin; Shi, Hui; Wang, Lei; Hu, Zhongyan; Li, Yifei; Xu, Xianxiu

doi:10.1002/adsc.201801103

Cited by 19 publications

(19 citation statements)

References 45 publications

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“…The elimination of p ‐toluenesulfinic acid afforded the dihydropyrrolo[2,3‐ c ]quinoline 129 . The final step was an aerobic oxidative aromatization, to obtain the MQs 122 a – y [48] …”

Section: Total Synthesis Of Natural and Unnatural Marinoquinolines An...mentioning

confidence: 99%

“…Curiously, when the authors applied this protocol to a domino bicyclization between the chalcones 121 and isocyanoacetate, the reaction stopped at the quinoline derivative 128 . This suggests that the tosyl group is essential for the elimination step that precedes the oxidation [48] . In addition, the open flask conditions lead to aerobic dehydrogenation, which constitutes a green approach to obtain these heteroaromatic compounds [49] …”

Section: Total Synthesis Of Natural and Unnatural Marinoquinolines An...mentioning

confidence: 99%

“…[46] Another approach to marinoquinolines using TosMIC was reported by Dong and co-workers in 2019. [48] The authors described an efficient reaction between 2-methyleneaminochalcones 121 and TosMIC in the presence of DBU (Scheme 24a) to synthesize twenty five MQs (Scheme 24b) in yields ranging from 50% to78%. [48] Scheme 22.…”

Section: Total Synthesis Of Natural and Unnatural Marinoquinolines An...mentioning

confidence: 99%

“…[48] The authors described an efficient reaction between 2-methyleneaminochalcones 121 and TosMIC in the presence of DBU (Scheme 24a) to synthesize twenty five MQs (Scheme 24b) in yields ranging from 50% to78%. [48] Scheme 22. (a) Synthesis of 4-substituted pyrrolo[2,3-c]quinolines, (b) structure of 4-substituted pyrrolo[2,3-c]quinolines 112 a-m as reported by Penjarla and co-workers, and (c) structures of 4-substituted pyrrolo[2,3-c]quinolines 112 n-t containing a bromine atom or substituents at pyrrole/quinoline rings.…”

Section: Total Synthesis Of Natural and Unnatural Marinoquinolines An...mentioning

confidence: 99%

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The Chemistry and Biological Applications of 3H‐Pyrrolo[2,3‐c]quinolines and Marinoquinolines

et al. 2021

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The heterocyclic 3H‐pyrrolo[2,3‐c]quinoline system and its closely related natural products, the marinoquinolines, have been attracting considerable attention in recent years in view of its interesting chemistry and diverse biological activities. Known since 1924, only in 2006 were the 3H‐pyrrolo[2,3‐c]quinolines associated with the first marinoquinolines isolated from natural sources. Their architecture and biological activities such as antiplasmodial, anti‐proliferative, anti‐bacterial, antifungal, phosphodiesterase and AChE inhibitors, and as ion‐sensing have stimulated the development of new strategies to obtain the natural marinoquinolines and new 3H‐pyrrolo[2,3‐c]quinoline derivatives. This review details the recent synthesis and biological evaluation of natural and unnatural marinoquinolines and its 3H‐pyrrolo[2,3‐c]quinoline core.

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Section: Total Synthesis Of Natural and Unnatural Marinoquinolines An...mentioning

confidence: 99%

Section: Total Synthesis Of Natural and Unnatural Marinoquinolines An...mentioning

confidence: 99%

Section: Total Synthesis Of Natural and Unnatural Marinoquinolines An...mentioning

confidence: 99%

Section: Total Synthesis Of Natural and Unnatural Marinoquinolines An...mentioning

confidence: 99%

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The Chemistry and Biological Applications of 3H‐Pyrrolo[2,3‐c]quinolines and Marinoquinolines

et al. 2021

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“…The relative configuration of prototype compound was confirmed by single crystal X-ray diffraction method. [39]…”

Section: Synthesis Of Fused Heterocyclesmentioning

confidence: 99%

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

Kumar

2020

ChemistrySelect

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p‐tosylmethyl isocyanide (TosMIC) which is also known as van Leusen's reagent hold the three functionalized groups including the isocyanide and sulfonyl group and an alpha carbon which is acidic by nature. Tosyl set of this fortunate reagent acts as a good leaving group and assist the alpha carbon to contribute in a range of cyclization strategies. Exceptionally, TosMIC was also proved as a good sulfonylating and sulfomethylating reagent. TosMIC has proved as a powerful and versatile synthon and betrothed in the synthesis of broad range of heterocycles having pharmacological interest. This review is focused on synthetic utility of TosMIC in diverse range of heterocycles like five membered heterocycles, fused heterocycles, linked or tethered heterocycles, spiro compounds etc. It is also utilized for regio, chemo and stereoselective synthesis and production of sulfones and sulfinates. It serves as an important building block in various synthetic methodologies like multi component reaction, cyclization, domino, cascade and cycloaddition and metal catalysed reactions. Various new catalyst and novel methodologies were explored due to enormous use of this wonderful reagent.

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Selective Preparation of Pyrrolo[2,3‐c]tetrahydroquinolines and Indolo[3,2‐c]tetrahydroquinolines through N‐Arylation/Cycloaddition/Rearrangement Annulation Reactions of Alkynyl‐Tethered Oximes with Diaryliodonium Salts

Nie,

Pan,

Deng

et al. 2024

Adv Synth Catal

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We describe a selective preparation of a variety of functionalized pyrrolo[2,3‐c]tetrahydroquinolines and indolo[3,2‐c]tetrahydroquinolines in 40‐82% and 40‐80% yields from alkynyl‐tethered oximes with diaryliodonium triflates, respectively. The one‐pot reaction underwent N‐arylation, intramolecular [3+2] cycloaddition, selective [1.3] or [3,3]‐rearrangement of N‐O bond in total three steps. Experimental studies revealed that EtOAc solvent and copper(II)‐catalyst played crucial roles on the formation of these two tetrahydroquinoline scaffolds. Moreover, these two tetrahydroquinoline scaffolds could be converted into various tetrahydroquinoline building blocks by further transformations.

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Tandem Cyclization−Annulation of α‐Acidic Isocyanides with 2‐Methyleneaminochalcones: Synthesis of Pyrrolo[2,3‐c]quinoline Derivatives

Cited by 19 publications

References 45 publications

The Chemistry and Biological Applications of 3H‐Pyrrolo[2,3‐c]quinolines and Marinoquinolines

The Chemistry and Biological Applications of 3H‐Pyrrolo[2,3‐c]quinolines and Marinoquinolines

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

Selective Preparation of Pyrrolo[2,3‐c]tetrahydroquinolines and Indolo[3,2‐c]tetrahydroquinolines through N‐Arylation/Cycloaddition/Rearrangement Annulation Reactions of Alkynyl‐Tethered Oximes with Diaryliodonium Salts

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