Structure of 2-acetyl-3-aminobenzofuran

Bachechi, F.; Coiro, V. M.; Delfini, Maurizio; Settimj, Guido

doi:10.1107/s0108270188002793

Cited by 8 publications

(6 citation statements)

References 2 publications

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“…The geometry of the benzofuran ring is comparable to that found in other benzofuran derivatives [ 19 , 24 , 25 , 26 ]. Only the C5-C6 bond length in the benzene seems rather longer due to the substituent at C6 indicating a π-electron delocalization within this fragment of the molecule.…”

Section: Resultssupporting

confidence: 67%

Synthesis and Preliminary Evaluation of the Antimicrobial Activity of Selected 3-Benzofurancarboxylic Acid Derivatives

et al. 2010

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Halogen derivatives of selected 3-benzofurancarboxylic acids were prepared using 6-acetyl-5-hydroxy-2-methyl-3-benzofuranocarboxylic acid as starting material. 1H-NMR spectra were obtained for all of the synthesized structures, and for compound VI, an X-ray crystal structure was also obtained. All derivatives were tested for antimicrobial activity against a selection of Gram-positive cocci, Gram-negative rods and yeasts. Three compounds, III, IV, and VI, showed antimicrobial activity against Gram-positive bacteria (MIC 50 to 200 μg/mL). Compounds VI and III exhibited antifungal activity against the Candida strains C. albicans and C. parapsilosis (MIC – 100 μg/mL).

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Section: Resultssupporting

confidence: 67%

Synthesis and Preliminary Evaluation of the Antimicrobial Activity of Selected 3-Benzofurancarboxylic Acid Derivatives

et al. 2010

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“…In the reported structure the O1-C2 distance is 1.385 (3) Å and it is similar to 1.385 Å found in 2-acetylbenzo(b)furan (Thiruvalluvar et al, 2003). However, the substituted compounds: [2-acetyl-3-(benzoylamino)-1-benzofuran (Ocak Ískeleli et al, 2005), 2-acetyl-3-aminobenzofuran (Bachechi et al, 1988), and 1-(3-amino-1-benzofuran-2-yl)-2-mesitylethanone (Arıcı et al, 2004) reveal somewhat longer bond distances of 1.403-1.411 Å.…”

Section: S1 Commentsupporting

confidence: 73%

“…For related literature, see: Arıcı et al (2004); Bachechi et al (1988); Fothergill et al (1977); Gareth (2001); Ocak Ískeleli et al (2005); Narimatsu et al (2003); Tanis et al (2006); Thiruvalluvar et al (2003); Weerawarna et al (1991); Zaidlewicz et al (2005).…”

Section: Related Literaturementioning

confidence: 99%

1-(1-Benzofuran-2-yl)-2-chloroethanone

2007

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Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.004 Å; R factor = 0.086; wR factor = 0.165; data-to-parameter ratio = 23.1.The title compound, C 10 H 7 ClO 2 , was synthesized from 1-benzofuran-2-ylethanone by chlorination with thionyl chloride. The benzofuran ring system and the carbonyl group are coplanar. The carbonyl group is in a syn position relative to both the O atom of the benzofuran ring and the Cl atom. C-HÁ Á ÁO contacts are found between the methylene group and carbonyl O atom. Molecules related by a centre of symmetry are involved ininteractions, with distances between the centroids of the furan rings of 3.785 (3) Å .

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“…A one-step route to 2-acetyl-3-amino [1]benzothiophene (10) is available 5 ; this product was obtained in 80% yield after a 16 h reaction time (see Supplementary Material file, p. S2). Since the structure of the corresponding 2-acetyl-3-amino [1]benzofuran has been reported, 6 the X-ray crystal structure of 10 was obtained for comparison (Fig. 1); there are two molecules in the asymmetric unit (data for the second molecule and the benzofuran equivalent are shown in Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…Unfortunately, application of the method to the quinoline analogue (6) gave the dinitrile (7) as the major product. We believe this product is formed via a known nitrene insertion in the hetero ring 4 , and subsequent rearrangements in which the elimination of ketene is the final step.…”

Section: Methodsmentioning

confidence: 99%

Flash vacuum pyrolysis of 2-acetyl-3-azido[1]benzothiophene

Gaywood¹,

McNab²,

McNab³

2020

Arkivoc

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Flash vacuum pyrolysis (FVP) of 2-acetyl-3-azido [1]benzothiophene at 300 °C provides 3-methyl [1]benzothieno[3,2-c]isoxazole (72%). At higher temperatures, the heteroindoxyl 1,2-dihydro[1]benzothieno[3,2-b]pyrrol-3-one was obtained in low yield (ca. 10%). The heteroindoxyl exists as a mixture of keto and enol forms in DMSO solution. Because of the easy oxidative dimerisation of these products to indigotin (and its heteroanalogues), such reactions are excellent examples of the synthetic advantages of FVP with the monomeric products conveniently generated under vacuum in a solvent -free, air-free environment.

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Structure of 2-acetyl-3-aminobenzofuran

Cited by 8 publications

References 2 publications

Synthesis and Preliminary Evaluation of the Antimicrobial Activity of Selected 3-Benzofurancarboxylic Acid Derivatives

Synthesis and Preliminary Evaluation of the Antimicrobial Activity of Selected 3-Benzofurancarboxylic Acid Derivatives

1-(1-Benzofuran-2-yl)-2-chloroethanone

Flash vacuum pyrolysis of 2-acetyl-3-azido[1]benzothiophene

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