Furan ring opening–indole ring closure: SnCl2-induced reductive transformation of difuryl(2-nitroaryl)methanes into 2-(2-acylvinyl)indoles

Uchuskin, Maxim G.; Molodtsova, Natalia V.; Абаев, Владимир Т.; Trushkov, Igor V.; Бутин, А. В.

doi:10.1016/j.tet.2012.03.069

Cited by 32 publications

(3 citation statements)

References 80 publications

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“…It is noteworthy that reduction of aromatic nitro compounds with metals in protic solvents such as alcohols is usually presumed to proceed by way of hydroxylamine‐like intermediates .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anti‐proliferative Activity of Novel Polysubstitued Indazole Derivatives

Oulemda

Chicha

Allam

et al. 2018

Journal of Heterocyclic Chem

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A simple and efficient process is developed for the synthesis of new N‐(1‐alkyl‐3‐chloro‐4‐ethoxy‐1H‐indazol‐5‐yl)‐arylsulfonamides 4a–d and N‐(1‐alkyl‐3‐chloro‐1H‐indazol‐5‐yl)‐arylsulfonamides 5a–d through the reduction of 1‐alkyl‐3‐chloro‐5‐nitroindazoles 2a,b with SnCl2 in ethanol followed by coupling the corresponding amine with arylsulfonyl chlorides in pyridine. All the newly synthesized compounds have been characterized by elemental analysis and spectroscopic data. Some compounds were tested for their in vitro antiproliferative activities against two selected human cancer cell lines A2780 and A549. Among all of these derivatives, compound 5d showed the most potent antiproliferative activity against A2780 (IC50 = 5.47 ± 1.45 μM) and A549 (IC50 = 7.73 ± 1.66 μM) cell lines.

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“…It is noteworthy that reduction of aromatic nitro compounds with metals in protic solvents such as alcohols is usually presumed to proceed by way of hydroxylamine‐like intermediates .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anti‐proliferative Activity of Novel Polysubstitued Indazole Derivatives

Oulemda

Chicha

Allam

et al. 2018

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

show abstract

“…The reduction of aromatic nitro compounds with metals in protic solvents such as alcohols is usually presumed to proceed by way of hydroxylamine-like intermediates [13,[22][23][24][25] .…”

Section: Resultsmentioning

confidence: 99%

SnCl₂/EtOH-Mediated Synthesis of Novel 4-Ethoxy- and 4-Chloroindazoles Bearing Sulfonamide Moieties

Chicha

Bouissane

Ammari

et al. 2015

Synthetic Communications

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The treatment of N-alkyl-5-nitroindazole with stannous chloride in ethanol gave after coupling of the obtained amines with arylsulfonyl chloride in pyridine the new 4-ethoxyand 4-chloroindazoles bearing sulfonamide in moderate to good yields. Chlorination and ethoxylation of indazole is observed during the reduction of the nitro group with anhydrous SnCl 2 in ethanol. The influence of the N-alkylation in N-1 and N-2 position of 5-nitroindazole on the reduction is investigated. The presence of ethoxy group and chlorine atom at position C-4 of indazole is confirmed by X-ray diffraction analysis of compounds 7a and 8a

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“…While the cyclization of malonate 12h was determined not to be diastereoselective (see Table , entry 8), heteroatoms could be incorporated into the tether to smoothly afford more-complex heterocycles such as benzo-1,3-oxazine 13i and dihydroquinazoline 13j (Table , entries 9 and 10). Beyond malonate and 2-pyridylacetic acid ethyl esters, enolizable nuclophiles such as 1,3-dimethylbarbituric acid-derived 12k and 1,3-indanedione-derived 12l smoothly formed new sp 3 -C–N bonds (Table , entries 11 and 12), and even difuran 12m underwent reductive cyclization and ring-opening to give indole 13m (see Table , entry 13) . These studies established the generality of this reductive cyclization method for the construction of a variety of partially saturated N -heterocyclic compounds from simple ortho -substituted nitroarenes.…”

mentioning

confidence: 99%

Intramolecular Pd-Catalyzed Reductive Amination of Enolizable sp³-C–H Bonds

et al. 2019

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A palladium-catalyzed reductive cyclization of nitroarenes has been designed to construct sp3-C–NHAr bonds from sp3-C–H bonds by using an enolizable nucleophile to intercept a nitrosoarene intermediate. Exposure of ortho-substituted nitroarenes to 5 mol % of Pd(OAc)2 and 10 mol % of phenanthroline under 2 atm of CO constructs partially saturated 5-, 6-, or 7-membered N-heterocycles using α-pyridyl carboxylates, malonates, 1,3-dimethylbarbituric acid, 1,3-diones, or difurans as the nucleophile.

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Furan ring opening–indole ring closure: SnCl2-induced reductive transformation of difuryl(2-nitroaryl)methanes into 2-(2-acylvinyl)indoles

Cited by 32 publications

References 80 publications

Synthesis and Anti‐proliferative Activity of Novel Polysubstitued Indazole Derivatives

Synthesis and Anti‐proliferative Activity of Novel Polysubstitued Indazole Derivatives

SnCl₂/EtOH-Mediated Synthesis of Novel 4-Ethoxy- and 4-Chloroindazoles Bearing Sulfonamide Moieties

Intramolecular Pd-Catalyzed Reductive Amination of Enolizable sp³-C–H Bonds

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Furan ring opening–indole ring closure: SnCl2-induced reductive transformation of difuryl(2-nitroaryl)methanes into 2-(2-acylvinyl)indoles

Cited by 32 publications

References 80 publications

Synthesis and Anti‐proliferative Activity of Novel Polysubstitued Indazole Derivatives

Synthesis and Anti‐proliferative Activity of Novel Polysubstitued Indazole Derivatives

SnCl2/EtOH-Mediated Synthesis of Novel 4-Ethoxy- and 4-Chloroindazoles Bearing Sulfonamide Moieties

Intramolecular Pd-Catalyzed Reductive Amination of Enolizable sp3-C–H Bonds

Contact Info

Product

Resources

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SnCl₂/EtOH-Mediated Synthesis of Novel 4-Ethoxy- and 4-Chloroindazoles Bearing Sulfonamide Moieties

Intramolecular Pd-Catalyzed Reductive Amination of Enolizable sp³-C–H Bonds