Synthesis of 1-azaxanthones by condensation of 1,3-bis(trimethylsilyloxy)-1,3-butadienes with 3-(cyano)benzopyrylium triflates and subsequent domino ‘retro-Michael/nitrile-addition/heterocyclization’ reaction

Rashid, Muhammad A.; Rasool, Nasır; Appel, Bettina; Adeel, Muhammad; Karapetyan, Vahuni; Mkrtchyan, Satenik; Reinke, Helmut; Fischer, Christine; Langer, Peter

doi:10.1016/j.tet.2008.02.105

Cited by 21 publications

(12 citation statements)

References 17 publications

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“…Herein again, we found that treating 3-nitroacetylquinolinone 4 with chromone-3-carbonitrile (15) 19 The transformation of 4 into 14 can be regarded as a domino "Michael/retro-Michael/nitrile-addition/ cyclocondensation" as shown in Scheme 7. 22 The combination of the pyrazole or the pyrimidine nucleus with the quinoline moiety, in one molecular framework, is reported in the literature to possess biological activity. [23][24][25] Herein, the nitroacetyl derivative 4 was allowed to react with some nucleophilic reagents.…”

Section: Resultsmentioning

confidence: 99%

Studies on the chemical behavior of 3-(nitroacetyl)-1-ethyl-4-hydroxyquinolin-2(1H)-one towards some electrophilic and nucleophilic reagents

Ibrahim¹,

Hassanin²,

Gabr³

et al. 2012

J. Braz. Chem. Soc.

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Uma variedade de sistemas heterocíclicos contendo o sistema 1-etilquinolin-2(1H)-ona, foi preparada a partir da reação de 3-(nitroacetil)-1-etil-4-hidroxiquinolin-2(1H)-ona com alguns reagentes eletrofílicos e nucleofílicos. Além da sua ciclização para 5-etil-2-(hidroxiimino)-2,3,4,5-tetrahydrofuro[3,2-c]quinolina-3,4-diona, o composto 3-(nitroacetil)-1-etil-4-hidroxiquinolina-2(1H)-ona foi bromado, clorado, formilado, acetilado, e condensado com cromona-3-carbonitrila e 2-amino-3-formilcromona. Alguns novos pirazolo [4,3-c]

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Section: Resultsmentioning

confidence: 99%

Studies on the chemical behavior of 3-(nitroacetyl)-1-ethyl-4-hydroxyquinolin-2(1H)-one towards some electrophilic and nucleophilic reagents

Ibrahim¹,

Hassanin²,

Gabr³

et al. 2012

J. Braz. Chem. Soc.

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“…Treatment of chromone-3-carbonitrile (30) active methylene compounds 31 in ethanol containing triethylamine afforded dibenzo[b,d]pyran-6-ones 32 (Scheme 15). 49 Scheme 15…”

Section: From Chromone-3-carbonitrilesmentioning

confidence: 99%

Chemical Transformation of Chromones into Coumarins

Badran¹,

Ahmed²,

Ibrahim³

2021

HETEROCYCLES

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“…It should be noted that the 3-cyanochromones react similarly with C-nucleophiles [31][32][33][34]. Recently obtained data has shown that these compounds are highly active and promising substrates for preparing a wide range of novel heterocycles with potential biological activity.…”

Section: Reactions Of 3-cyanochromones With Hydroxylaminementioning

confidence: 99%