Selective Synthesis of Quinolines and Indoles: Sulfur‐Assisted or Selenium‐Catalyzed Reaction of β‐(2‐Nitrophenyl)‐α,β‐unsaturated Ketones with Carbon Monoxide

Umeda, Rui; Kouno, Hiroshi; Kitagawa, Takayuki; Okamoto, Tomohiro; Kawashima, Keisuke; Mashino, Tsukasa; Nishiyama, Yutaka

doi:10.1002/hc.21189

Cited by 18 publications

(7 citation statements)

References 39 publications

(16 reference statements)

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“…We found that the chalcone with the nitro group at the ortho position develops the strongest anti-inflammatory protective effect, whereas the chalcone with the nitro group at the para position, showed the smallest effect [14]. Another important aspect of Crystals 2021, 11, 1589 2 of 12 some nitro chalcones is that they can be used as intermediates for synthesizing various heterocyclic compounds like indoles, thioaurones, carbazoles, sultams, benzothiophenes, quinolines and indolin-3-ones [15][16][17][18][19][20][21][22][23]. On the other hand, the nitro chalcones also find application as chemosensors for anion sensing [24].…”

Section: Introductionmentioning

confidence: 94%

Synthesis, Crystal Structures, and Molecular Properties of Three Nitro-Substituted Chalcones

et al. 2021

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Three functionalized chalcones containing combinations of nitro functional groups have been synthesized via Claisen-Schmidt condensation between 2-nitroacetophenone and nitrobenzaldehyde, and the crystal structures obtained ((E)-1,3-bis(2-nitrophenyl)prop-2-en-1-one, 1a, (E)-1-(2-nitrophenyl)-3-(3-nitrophenyl)prop-2-en-1-one, 1b and (E)-1-(2-nitrophenyl)-3-(4-nitrophenyl)prop-2-en-1-one, 1c), C15H10N2O5, are reported. Compounds 1a and 1c crystallized in the triclinic centrosymmetric space group P1¯, whereas compound 1b crystallized in the orthorhombic space group Pbca. The X-ray analysis reveals that structures 1a and 1b exhibits s-trans conformation, whereas structure 1c exists in s-cis conformation, concerning the olefinic double bonds. In addition, the results show that the position of the nitro substituent attached to the aromatic B-ring has a direct effect on the molecular coplanarity of these compounds. The Hirshfeld surface analysis suggests that the non-covalent π-π stacking interactions are the most important contributors for the crystal packing of 1a and 1b. In 1c, the crystal packing is mainly stabilized by weak intermolecular C―H···O interactions due to the planar nature of the molecule.

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Section: Introductionmentioning

confidence: 94%

Synthesis, Crystal Structures, and Molecular Properties of Three Nitro-Substituted Chalcones

et al. 2021

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“…Nishiyama et al. developed a simple and selective synthetic method for quinolines 643 in moderate to good yields by the reductive cyclization of β‐(2‐nitrophenyl)‐α,β‐unsaturated ketones 642 with carbon monoxide, elemental sulfur and water (Scheme ) …”

Section: Sulfur As Catalystmentioning

confidence: 99%

Recent Advances in Organic Reactions Involving Elemental Sulfur

2017

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Elemental sulfur hasb een known since Antiquity and found widespread applications in the preparation of black gunpowder,t he synthesis of sulfuric acid as well as other sulfur-containing compounds,a nd the vulcanization of rubber.O ver the last several years,wehave come to better understand its properties andd iscover more applications of elementals ulfuri ns ynthetic organic chemistry.T his review summarizes the advancesf rom 2000i nt he construction of organic molecules using elemental sulfur via sulfuration, oxidation, reduction and redox condensation processes.

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“…(11)] [110] and quinolines from 2-nitrochalcones [Eq. (12)] [111,112] have been reported. In the latter case, the intermediacy of the aniline obtained via WGSR reduction was suggested by a set of clever competition experiments.…”

Section: The Water-gas Shift Reaction In Organic Synthesismentioning

confidence: 99%

Harnessing the Power of the Water‐Gas Shift Reaction for Organic Synthesis

Ambrosi

Denmark

2016

Angew Chem Int Ed

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Since its original discovery over a century ago, the water-gas shift reaction (WGSR) has played a crucial role in industrial chemistry, providing a source of H2 to feed fundamental industrial transformations such as the Haber–Bosch synthesis of ammonia. Although the production of hydrogen remains nowadays the major application of the WGSR, the advent of homogeneous catalysis in the 1970s marked the beginning of a synergy between WGSR and organic chemistry. Thus, the reducing power provided by the CO/H2O couple has been exploited in the synthesis of fine chemicals; not only hydrogenation-type reactions, but also catalytic processes that require a reductive step for the turnover of the catalytic cycle. Despite the potential and unique features of the WGSR, its applications in organic synthesis remain largely underdeveloped. The topic will be critically reviewed herein, with the expectation that an increased awareness may stimulate new, creative work in the area.

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Selective Synthesis of Quinolines and Indoles: Sulfur‐Assisted or Selenium‐Catalyzed Reaction of β‐(2‐Nitrophenyl)‐α,β‐unsaturated Ketones with Carbon Monoxide

Cited by 18 publications

References 39 publications

Synthesis, Crystal Structures, and Molecular Properties of Three Nitro-Substituted Chalcones

Synthesis, Crystal Structures, and Molecular Properties of Three Nitro-Substituted Chalcones

Recent Advances in Organic Reactions Involving Elemental Sulfur

Harnessing the Power of the Water‐Gas Shift Reaction for Organic Synthesis

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