Potassium <i>tert</i>‐Butoxide‐Promoted Synthesis of 1‐Aminoisoquinolines from 2‐Methylbenzonitriles and Benzonitriles under Catalyst‐Free Conditions

Feng, Jianbo; Wu, Xiao‐Feng

doi:10.1002/adsc.201600169

Cited by 29 publications

(16 citation statements)

References 38 publications

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“…The reactions conditions shows good applicability to wide range of substrates in synthesizing 1-aminoisoquinolines (Scheme 287). [287] According to the proposed mechanism, the reaction is expected to begin with KOtBu mediated proton abstraction Gutiérrez group have reported heterocyclization that involves α-benzyl TosMIC derivatives 471 and different electrophiles 472 towards the synthesis of 1substituted isoquinolines 473 (Scheme 289). [288] Salfeena et al reported BF 3 -etherate mediated onepot synthesis of 5,6-dihydroisoquinoline derivatives 475 from readily available α,β-unsaturated ketones/ arylidene ketones 474, substituted nitriles 449 and aryl acetylenes 114.…”

Section: Non-metal Catalyzed Isoquinoline Synthesis and Other Methodsmentioning

confidence: 99%

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

2020

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In the past decades, an enormous number of reports have been dedicated towards the synthesis of nitrogen containing heterocycles. This immense interest have emerged owing to their wide varieties of pharmacological activities. The present review focused on the synthesis of isoquinoline derivatives, a family of N-heterocycles showing a broad range of structural diversity, biological and pharmaceutical activities. The progress on their synthetic strategies using versatile approaches are discussed in details.

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Section: Non-metal Catalyzed Isoquinoline Synthesis and Other Methodsmentioning

confidence: 99%

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

2020

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“…Quinoline and quinazolinones molecules (Table 1, 2) were synthesized during the original synthetic methodologies studies (Shen et al ., 2015, 2016; Feng and Wu, 2016). The purity of each compound was greater 99% and confirmed by gas chromatography-mass spectrometry and nuclear magnetic resonance (1H-NMR and 13C-NMR).…”

Section: Methodsmentioning

confidence: 99%

Novel Isoquinolinamine and Isoindoloquinazolinone Compounds Exhibit Antiproliferative Activity in Acute Lymphoblastic Leukemia Cells

Roolf

Saleweski

Stein

et al. 2019

Biomolecules & Therapeutics

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Nitrogen-containing heterocycles such as quinoline, quinazolinones and indole are scaffolds of natural products and have broad biological effects. During the last years those structures have been intensively synthesized and modified to yield new synthetic molecules that can specifically inhibit the activity of dysregulated protein kinases in cancer cells. Herein, a series of newly synthesized isoquinolinamine (FX-1 to 8) and isoindoloquinazolinone (FX-9, FX-42, FX-43) compounds were evaluated in regards to their anti-leukemic potential on human B- and T-acute lymphoblastic leukemia (ALL) cells. Several biological effects were observed. B-ALL cells (SEM, RS4;11) were more sensitive against isoquinolinamine compounds than T-ALL cells (Jurkat, CEM). In SEM cells, metabolic activity decreased with 10 μM up to 26.7% (FX-3), 25.2% (FX-7) and 14.5% (FX-8). The 3-(p-Tolyl) isoquinolin-1-amine FX-9 was the most effective agent against B- and T-ALL cells with IC50 values ranging from 0.54 to 1.94 μM. None of the tested compounds displayed hemolysis on erythrocytes or cytotoxicity against healthy leukocytes. Anti-proliferative effect of FX-9 was associated with changes in cell morphology and apoptosis induction. Further, influence of FX-9 on PI3K/AKT, MAPK and JAK/STAT signaling was detected but was heterogeneous. Functional inhibition testing of 58 kinases revealed no specific inhibitory activity among cancer-related kinases. In conclusion, FX-9 displays significant antileukemic activity in B- and T-ALL cells and should be further evaluated in regards to the mechanisms of action. Further compounds of the current series might serve as templates for the design of new compounds and as basic structures for modification approaches.

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“…Wu and Feng disclosed a novel procedure toward 1‐aminoisoquinolines via the reaction of o ‐toluenenitriles and benzonitriles upon treatment with potassium tert ‐butoxide. However, these approaches were difficult to construct multisubstituted 1‐aminoisoquinolines . Recently, our group has been devoted to the construction of 4 H ‐pyran/1,4‐dihydropyridine‐based solid‐state fluorescence stimulus‐responsive materials using 2,6‐dimethyl‐4‐pyrone ( 1 ) as the starting material (Scheme ) .…”

Section: Introductionmentioning

confidence: 99%

Metal‐Free Facile Synthesis of Multisubstituted 1‐Aminoisoquinoline Derivatives with Dual‐State Emissions

Zhang

Zhou

Wang

et al. 2020

Chemistry An Asian Journal

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Although isoquinoline is a good traditional fluorescent structural unit, most of its derivatives emit fluorescence in solution and a few of them can emit solidstate fluorescence as well. Herein, a series of multisubstituted 1-aminoisoquinoline derivatives were synthesized by a simple reaction of a readily available 4H-pyran derivative and secondary amines. The reaction had advantages of metalfree, mild conditions, simple operation, and good yields, which was realized by a ring-opening and sequential ringclosing mechanism. These 1-aminoisoquinoline derivatives were found to exhibit interesting dual-state emissions. In the solution, they emitted strong blue fluorescence at about 458 nm. In the solid state, they emitted solid-state blue fluorescence at 444-468 nm with high fluorescence quantum yields of 40.3-98.1%. Crystal structural analyses indicated that solid-state emissions of these compounds originated from twisted molecular conformations and the resultant loose stacking arrangements. Furthermore, their solid-state fluorescence wavelengths were demonstrated to depend on molecular conformations rather than stacking arrangements. The discovery of these 1-aminoisoquinolines with multiple reaction sites provides new possibilities for the development of solid-state fluorescent materials based on the traditional isoquinoline skeleton.

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Potassium tert‐Butoxide‐Promoted Synthesis of 1‐Aminoisoquinolines from 2‐Methylbenzonitriles and Benzonitriles under Catalyst‐Free Conditions

Abstract: Herein a practical and efficient protocol for preparing a range of aminoisoquinolines is reported. Various aminoisoquinolines were prepared in moderate to good yields from the corresponding 2‐methylbenzonitriles and benzonitriles upon treatment with potassium tert‐butoxide.

Cited by 29 publications

References 38 publications

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

Comprehensive Strategies for the Synthesis of Isoquinolines: Progress Since 2008

Novel Isoquinolinamine and Isoindoloquinazolinone Compounds Exhibit Antiproliferative Activity in Acute Lymphoblastic Leukemia Cells

Metal‐Free Facile Synthesis of Multisubstituted 1‐Aminoisoquinoline Derivatives with Dual‐State Emissions

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