Bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone: a new-type azafulvenium reactivity of indole

Kılıç, Hamdullah; Bayındır, Sinan; Erdogan, Esra; Çınar, Sesil Agopcan; Konuklar, F. A. S.; Bali, Semiha Kevser; Saraçoğlu, Nurullah; Avi̇yente, Vi̇ktorya

doi:10.1039/c7nj01987d

Cited by 7 publications

(2 citation statements)

References 95 publications

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“…Based on the information obtained from controlled experiments and literature reports, we proposed a possible reaction mechanism for the S–N bond construction (Scheme ). In the presence of Cs 2 CO 3 , substrate A would be converted to B , which made the S atom more nucleophilic and therefore readily reacted with PIDA to form the reactive intermediate C .…”

Section: Resultsmentioning

confidence: 99%

Selective Construction of C–S/S–N Bonds from N-Substituted O-Thiocarbamates and Indoles under Transition-Metal-Free Conditions

Liu,

Hu,

et al. 2024

J. Org. Chem.

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A method for the selective construction of S−N/C(sp 2 )-S bonds using N-substituted O-thiocarbamates and indoles as substrates is reported. This protocol features good atom utilization, mild conditions, short reaction time, and wide substrate scope, which can provide a convenient path for the functionalization of indoles. In addition, the reaction could be scaled up on gram scale, showing potential application value in industry synthesis.

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Section: Resultsmentioning

confidence: 99%

Selective Construction of C–S/S–N Bonds from N-Substituted O-Thiocarbamates and Indoles under Transition-Metal-Free Conditions

Liu,

Hu,

et al. 2024

J. Org. Chem.

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“…1 H NMR (400 MHz, CDCl 3 ) δ 7.94 (ddd, J = 7.9, 1. 1-(Cyclohept-1-en-1-yl)-3-methyl-1H-indole (5a) 50 CAS 2122299−51−6. Synthesized according to the general procedure A.…”

Section: -Benzyl-1-(cyclohex-1-en-1-yl)-1h-indole (3o)mentioning

confidence: 99%

Synthesis of N-Alkenylated Heterocycles via T₃P-Promoted Condensation with Ketones

Balestri,

Beveridge,

Gising

et al. 2024

J. Org. Chem.

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Herein, we describe a convenient protocol for the synthesis of N-alkenylated heterocycles using abundant ketone electrophiles and T 3 P as a water scavenger under microwave irradiation. The method can be applied to a diverse range of NHheterocycles and ketones with good to excellent yields (up to 94%). This procedure is particularly attractive, as it is metal-and basefree, tolerates a variety of functional groups, and offers ease of product purification. The utility of the protocol was exemplified by synthesizing pharmaceutically relevant scaffolds containing the N-alkenyl motif and was further extended to a one-pot reductive amination sequence.

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The synthesis of N‐benzoylindoles as inhibitors of rat erythrocyte glucose‐6‐phosphate dehydrogenase and 6‐phosphogluconate dehydrogenase

Bayındır

Temel

Ayna

et al. 2018

J Biochem & Molecular Tox

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Glucose-6-phosphate dehydrogenase (G6PD) and 6-phosphogluconate dehydrogenase (6PGD) play an important function in various biochemical processes as they generate reducing power of the cell. Thus, metabolic reprogramming of reduced nicotinamide adenine dinucleotide phosphate (NADPH) homeostasis is reported to be a vital step in cancer progression as well as in combinational therapeutic approaches. In this study, N-benzoylindoles 9a--9d, which form the main framework of many natural indole derivatives such as indomethacin and N-benzoylindoylbarbituric acid, were synthesized through three easy and effective steps as an in vitro inhibitor effect of G6PD and 6PGD. The N-benzoylindoles inhibited the enzymatic activity with IC in the range of 3.391505 μM for G6PD and 2.19-990 μM for 6PGD.

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Bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone: a new-type azafulvenium reactivity of indole

Abstract: The bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone in one pot, to yield C3-cyclohexyl substituted indoles and 1,3-di(1H-indol-3-yl)benzene derivatives is reported for the first time.

Cited by 7 publications

References 95 publications

Selective Construction of C–S/S–N Bonds from N-Substituted O-Thiocarbamates and Indoles under Transition-Metal-Free Conditions

Selective Construction of C–S/S–N Bonds from N-Substituted O-Thiocarbamates and Indoles under Transition-Metal-Free Conditions

Synthesis of N-Alkenylated Heterocycles via T₃P-Promoted Condensation with Ketones

The synthesis of N‐benzoylindoles as inhibitors of rat erythrocyte glucose‐6‐phosphate dehydrogenase and 6‐phosphogluconate dehydrogenase

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Bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone: a new-type azafulvenium reactivity of indole

Abstract: The bismuth nitrate-promoted disproportionative condensation of indoles with cyclohexanone in one pot, to yield C3-cyclohexyl substituted indoles and 1,3-di(1H-indol-3-yl)benzene derivatives is reported for the first time.

Cited by 7 publications

References 95 publications

Selective Construction of C–S/S–N Bonds from N-Substituted O-Thiocarbamates and Indoles under Transition-Metal-Free Conditions

Selective Construction of C–S/S–N Bonds from N-Substituted O-Thiocarbamates and Indoles under Transition-Metal-Free Conditions

Synthesis of N-Alkenylated Heterocycles via T3P-Promoted Condensation with Ketones

The synthesis of N‐benzoylindoles as inhibitors of rat erythrocyte glucose‐6‐phosphate dehydrogenase and 6‐phosphogluconate dehydrogenase

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Synthesis of N-Alkenylated Heterocycles via T₃P-Promoted Condensation with Ketones