ChemInform Abstract: Molecular Structure of N‐Mesityl‐6H‐anthra(9,1‐bc)pyrrol‐6‐one.

Gridunova, G. V.; Shklover, V. E.; Struchkov, Yu. T.; Alimova, R. A.; Gorelik, M. V.

doi:10.1002/chin.198843189

Cited by 1 publication

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“…Intensities of 1469 independent reflections were measured at room temperature; unit cell parameters: a = 28.016 (11), b = 42.40(3), c = 5.013 (3) Å; V = 5955(5) Å 3 ; Z = 16; d calc = 1.318 g/cm 3 ; μ(MoK α ) = 0.081 mm -1 ; space group Fdd2. The structure was solved by the direct method using SHELXS-97 software package and was refined with respect to all F 2 hkl in anisotropic approximation for non-hydrogen atoms and isotropic approximation (riding model) for hydrogen atoms using SHELXS-97 software.…”

Section: Methodsmentioning

confidence: 99%

“…The reduction product displayed no paramagnetic properties and was assigned the structure of 2-phenylanthra[9,1-bc]pyrrol-6-one (VII). The yield of 1.374(8)0 C 5a -C 5 1.411(12) C 10a -C 10b 1.401(11) O 1 -C 6 1.270(7)0 C 5a -C 6 1.434(12) C 10s -C 10b 1.397(10) C 2a -C 3 1.410(13) C 6a -C 7 1.380(12) C 11 -C 16 1.354(16) C 2a -C 10s 1.418(11) C 6a -C 10a 1.451(9)0 C 11 -C 12 1.389(13) C 2a -C 2 1.419(9)0 C 6a -C 6 1.474(12) C 12 -C 13 1.383(12) C 2 -C 11 1.454(10) C 7 -C 8 1.417(14) C 13 -C 14 1.384(18) C 3 -C 4 1.376(10) C 8 -C 9 1.372 (9) (7) C 10c C 2a C 2 106.6(8) O 1 C 6 C 6a 119.6(8) C 10c C 10b C 10a 121.9(6) N 1 C 2 C 2a 105.9(7) C 5a C 6 C 6a 117.6(6) C 9 C 10 C 10a 122.6(7) N 1 C 2 C 11 122.7(7) C 6a C 7 C 8 121.0(7) C 16 C 11 C 12 116.6(8) C 2a C 2 C 11 131.3(9) C 9 C 8 C 7 119.5(9) C 16 C 11 C 2 121.8(9) C 4 C 3 C 2a 120.2(9) C 10 C 9 C 8 120.5(9) C 12 C 11 C 2 121.5(9) C 3 C 4 C 5 121.9(9) C 10 C 10a C 10b 126.9(6) C 13 C 12 C 11 0120.2(12) C 10c C 5a C 5 115.4(8) C 10 C 10a C 6a 117.5(8) C 14 C 13 C 12 0121.5(12) C 10c C 5a C 6 118.1(7) C 10b C 10a C 6a 115.6(7) C 15 C 14 C 13 0118.8(10)…”

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confidence: 97%

“…Unlike compound VII, the 2,4,6-trimethylStructure of the molecule of 2-phenylanthra[9,1-bc]pyrrol-6-one (VII) according to the X-ray diffraction data. phenyl group in structurally related 1-(2,4,6-trimethylphenyl)-6H-anthra[9,1-bc]pyrrol-6-one [11] is turned through an angle of 79.5° from the plane of the tetracyclic skeleton. Molecules VII in crystal are linked in "head-to-tail" mode through intermolecular hydrogen bonds N 1 -H · · · O 1 , giving rise to chains oriented along the a + c and a -c axes.…”

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Synthesis and structure of 2-phenylanthra[9,1-bc]pyrrol-6-one

et al. 2010

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Reduction of anti-1-benzoylanthraquinone oxime gave 2-phenylanthra[9,1-bc]pyrrol-6-one whose structure was determined by X-ray analysis. The molecule of 2-phenylanthra[9,1-bc]pyrrol-6-one is almost planar, and its crystalline structure is characterized by head-to-tail chains formed via intermolecular hydrogen bonds N-H · · · O. 9,10-Anthraquinone derivatives attract strong interest for both science and technics. They are traditionally used for the manufacture of synthetic dyes, but in the recent time 9,10-anthraquinones have found new applications, in particular as biologically active compounds, analytical reagents, luminophores, components of liquid crystalline compositions, photographic materials, etc.[1]. The 2-phenylanthra[9,1-bc]pyrrol-6-one system (A) is a peri-fused antrhaquinone derivative with 1,10-anthraquinoid structure. The presence of a fused pyrrole ring and anthrone fragment with unusual ana-quinoid bond configuration suggests high reactivity of such system.First attempts to synthesize anthra[9,1-bc]pyrrol-6-ones with no substituent on the nitrogen atom were reported long ago. Sholl et al. [2] showed that anthra-[9,1-bc]pyrrole derivatives can be obtained by reduction of 1-aroylanthraquinonone oximes. However, the products were assigned anthroxyl radical structure B, and later, aminyl radicals C [3]. According to [4, 5], such radicals are generated by reduction of 1-cyanoanthraquinone or in the cyclization of 1-aminomethyl derivatives of 2-hydroxyanthraquinone which are obtained in turn by alkaline hydrolysis of 1-phthalimidomethyl-or trichloroacetylaminomethyl-2-hydroxyanthraquinones. After repeated experiments, Sholl and Muller [6] concluded that the reduction products of 1-aroylanthraquinone oximes are non-radical species and that they have structure A with 1,10-anthraquinoid bond distribution; however, no rigorous proofs for the

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Section: Methodsmentioning

confidence: 99%