Direct Synthesis of Pyrrolo[3,4‐<i>c</i>]quinolines from the Domino Reaction of Tosylmethyl Isocyanides and Aminochalcones

Hu, Zhongyan; Li, Yifei; Pan, Ling; Xu, Xianxiu

doi:10.1002/adsc.201400468

Cited by 23 publications

(5 citation statements)

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“…Both electron-donating and electron-withdrawing groups used, gave the desired products in high yields. 226 The mechanism involved formation of carbanion 416 and its cyclization to form intermediate 417 followed by H-shi and cyclization of 418 (Scheme 107).…”

Section: Isocyanide-based Synthesis Of Heterocyclesmentioning

confidence: 99%

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

2016

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Section: Isocyanide-based Synthesis Of Heterocyclesmentioning

confidence: 99%

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

2016

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“…This may be due to the formation of the cyclization side product between the amino group on the A ring and the aromatic B ring, which is very difficult to separate from the target compound by flash column chromatography as the two molecules have the same retention time. The cyclization of 2'-aminochalcones has been reported before [ 25 ]. Moreover, the different attempts pointed out that both time and temperature influence the hydrolysis reaction.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structure, and antioxidant activity of methoxy- and hydroxyl-substituted 2'-aminochalcones

et al. 2016

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Three 2'-aminochalcone derivatives (E)-1-(2-aminophenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one, (E)-1-(2-aminophenyl)-3-(3,4-dihydroxyphenyl)prop-2-en-1-one, and (E)-1-(2-amino-4,5-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one, have been synthesized, characterized, and tested in vitro in order to assess their antioxidant activity. All compounds were characterized on the basis of 1H NMR, 13C NMR, ESI-mass spectrometry, FT-IR, UV/Vis, and elemental analysis. The X-ray crystal structures of (E)-1-(2-aminophenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one and (E)-1-(2-amino-4,5-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one were successfully determined showing a planar molecule geometry. Studies on the biological properties including test of free radical scavenging ability (DPPH test) and superoxide dismutase mimetic activity were performed. The results indicate that the aminochalcone carrying two hydroxyl functionalities in adjacent meta and para position exhibits a stronger antioxidant activity than the other derivatives.Graphical abstractElectronic supplementary materialThe online version of this article (doi:10.1007/s00706-016-1812-9) contains supplementary material, which is available to authorized users.

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“…The simple, efficient, economical protocol had wide substrate scope and acquiescent to gram scale synthesis. [28] A mechanistic pathway for the domino synthesis of pyrroloquinolines is proposed as shown in SÀ J Ji and co-workers reported an efficient and applied synthetic approach to afford 2H-pyrrolo[3,4-c]quinoline derivatives 72 by the reaction of 2-aminoarylacrylates/2-aminochalcones 71 and tosylmethyl isocyanide in one pot as depicted in Scheme 40. Optimization study reveal that potassium tertiary butoxide in tetrahydro furan under heating is suitable for reaction.…”

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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Direct Synthesis of Pyrrolo[3,4‐c]quinolines from the Domino Reaction of Tosylmethyl Isocyanides and Aminochalcones

Abstract: A tandem formal [3+2] cycloaddition/cy-

Cited by 23 publications

References 50 publications

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

Isocyanide-based multicomponent reactions in the synthesis of heterocycles

Synthesis, structure, and antioxidant activity of methoxy- and hydroxyl-substituted 2'-aminochalcones

TosMIC: A Powerful Synthon for Cyclization and Sulfonylation

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